Two-Generation Toxicity Study of the Antioxidant Compound Propyl-Propane Thiosulfonate (PTSO).

Propyl-propane thiosulfonate (PTSO), an antioxidant organosulfur compound present in the genus Allium, has become a potential natural additive for food and feed, as well as a possible biopesticide for pest control in plants. A toxicological assessment is necessary to verify its safety for livestock, consumers, and the environment. As part of the risk assessment of PTSO, this study was designed to explore its potential reproductive toxicity in mice following the OECD 416 guideline. The investigation spans two generations to comprehensively evaluate potential reproductive, teratogenic, and hereditary effects. A total of 80 CD1 mice per sex and generation were subjected to PTSO exposure during three phases (premating, gestation, and lactation). This evaluation encompassed three dose levels: 14, 28, and 55 mg PTSO/kg b.w./day, administered through the feed. No clinical changes or mortality attributed to the administration of PTSO were observed in the study. Some changes in the body weight and food consumption were observed, but not related to sex or in a dose-dependent manner. The two parental generations (F0, F1) exhibited normal reproductive performance, and the offspring (F1 and F2) were born without any abnormalities. The serum sexual hormone levels (progesterone -P-, testosterone -T-, estradiol -E2-, follicular stimulating hormone -FSH-, and luteinizing hormone -LH-) were in a normal range. Although significant changes were observed in the sperm analysis in the case of F0 group, no variation was found for F1 group, and no alterations in fertility were recorded either. The absolute organ weights and relative organ weight/body weight and organ weight/brain weight ratios, and the complete histopathological study, showed no significant alterations in males and females for all the generations considered. Considering all the results obtained, PTSO is not considered a reproductive or developmental toxicant in mice under the assayed conditions. These results support the good safety profile of PTSO for its potential application in the agrifood sector.

Simultaneous determination of Allium compounds (Propyl propane thiosulfonate and thiosulfinate) in animal feed using UPLC-MS/MS.

Propyl-propane-thiosulfonate (PTSO) and Propyl-propane-thiosulfinate (PTS) are organosulfur compounds used to supplement the diet of livestock because of their beneficial effects on feed palatability, their antibacterial, anti-inflammatory, and antimethanogenic activities. Besides, antibiotic residues in the environment can be reduced by using these natural bioactive compounds. The objective of this study was to optimize the extraction parameters for the analysis of PTSO and PTS in feed matrices by performing a solid-liquid extraction and quantification by Ultra performance liquid chromatography coupled to tandem mass spectrometry (UPLC-MS/MS). Optimization was performed using the Response Surface Methodology on a Box-Behnken experimental design, optimizing the following parameters: solvent:sample ratios and evaporation temperature set for the rotary evaporator. The method was validated for 3 concentration levels for both PTSO (100, 500, 1000 ng g-1) and PTS (500, 1150, 2300 ng g-1). The highest recoveries of PTSO and PTS were obtained using 12.5 mL of 100% acetonitrile, stirring for 15 min, and an evaporation temperature of 20 °C. The validated method was further applied to detect and quantify these compounds in different feed matrices. In conclusion, this is the first study to simultaneously analyze PTSO and PTS at low concentrations, employing a sensitive technique such as UPLC-MS/MS.

Feasibility and cost of a telemedicine-based short-term plan for initial access in general dermatology in Andalusia, Spain.

BACKGROUND: In developed countries, health care delivery in dermatology is hampered by the low availability of dermatologists. OBJECTIVE: To analyze the feasibility of a teledermatology-based action plan to provide initial dermatologic care in areas with low availability of dermatologists. METHODS: A cross-sectional study describing the feasibility and cost of a 12-month action plan based on a store-and-forward teledermatology (TD) connecting primary care centers and a TD center. Teleconsultations from patients complaining of any cutaneous condition were included. The primary outcome measure was the percentage of patients not referred to the local dermatologist. RESULTS: Among the total of 15,523 teleconsultations attended in the TD-based action plan, 3360 (21.65%) required a face-to-face visit with a local dermatologist. In 32.32% (n = 5017) of the cases, a therapeutic and follow-up plan report was issued. The most common conditions managed were melanocytic nevi (15.63%, n = 2426), followed by seborrheic keratosis (14.89%, n = 2312), and actinic keratosis (8.65%, n = 1342). The average response time was 14.52 days (95% CI 14.35-15.23). The additional total investment in this action plan was $142,681.01, with a unit cost of 9.20$/patient. LIMITATIONS: Noncontrolled study. CONCLUSIONS: Experienced dermatologists working with store-and-forward TD can deliver a fast and effective response in health care areas with access limitations.

Late Electrocardiographic Changes in Patients With New-Onset Left Bundle Branch Block Following Transcatheter Aortic Valve Implantation.

This study sought to determine, in patients with new-onset persistent left bundle branch block (NOP-LBBB) after transcatheter aortic valve implantation (TAVI), the incidence and factors associated with (i) LBBB recovery and (ii) permanent pacemaker implantation (PPI) at 1-year follow-up. This was a multicenter study including 153 patients (mean age: 81 ± 5 years, 56% of women) with NOP-LBBB post-TAVI (balloon-expandable valve in 112 patients). Delta PR (ΔPR) and delta QRS (ΔQRS) were defined as the difference in PR and QRS length between baseline and hospital discharge ECG, and the relative ΔPR and ΔQRS as absolute ΔPR and ΔQRS divided by baseline PR and QRS length, respectively. The patients had a clinical visit and 12-lead ECG at 1-year follow-up. LBBB recovery was observed in 50 patients (33%), and 14 patients (9%) had advanced conduction disturbances requiring PPI during the follow-up period. No clinical or ECG variables were associated with LBBB recovery, including prosthesis type (self- or balloon-expandable valve, p = 0.563), QRS width at baseline/discharge or absolute/relative ΔQRS (p >0.10 for all). The presence of atrial fibrillation at baseline (0.026), a longer PR interval at discharge (0.009), and a longer absolute and relative ΔPR (p = 0.002 and p = 0.004, respectively) were associated with an increased risk of PPI at 1-year follow-up. In conclusion, NOP-LBBB post-TAVI resolved in one-third of patients at 1-year follow-up, but no clinical or ECG variables were associated with LBBB recovery. Conversely, a nonsinus rhythm at baseline and a longer ΔPR were associated with an increased risk of PPI within the year after TAVI.

Immediate and Long-Term Results of Drug-Eluting Stents in Mammary Artery Grafts.

UNLABELLED: Percutaneous intervention of a coronary graft is the treatment of choice when the graft fails. The objective is to report the long-term results of drug-eluting stents (DES) in mammary artery grafts (MAG). Patients who had been treated with DES for MAG in 27 centers were selected. The baseline and procedural clinical data were included prospectively, and the follow-up was performed with the patients, families, and medical records. Two hundred and sixty-eight patients were included: age 65.5 ± 10.1 years, diabetes 47.8%, ejection fraction 55.5 ± 14.9%. INDICATION: stable angina 28.4%, unstable angina 38.1%, non-ST-elevation myocardial infarction 21.6%, ST-elevation myocardial infarction 5.3%, and heart failure 6.7%; 1.19 ± 0.59 stents/patient were implanted measuring 18.8 ± 8.8 mm in length and 2.68 ± 0.35 mm in diameter. Rapamycin was used in 78 cases (29.1%), paclitaxel in 77 (28.7%), everolimus in 70 (26.1%), zotarolimus in 34 (12.7%), and biolimus in 9 (3.4%). All cases were successful except for 1 in which the patient died 30 minutes after the procedure. There were no other inhospital events. After a follow-up of 41 months (Q25: 23.7 to Q75: 57.8), 24 patients (9%) died of heart-related causes and 20 (7.5%) of noncardiac causes. Repeat revascularization was necessary in 31 cases, and in 1 additional patient, there was total occlusion, which was not treated. These 32 patients represented 11.9% of the total. In conclusion, the implantation of DES in MAG shows very high procedural success and also low long-term event rates.

Spanish Cardiac Catheterization and Coronary Intervention Registry. 21st official report of the Spanish Society of Cardiology Working Group on Cardiac Catheterization and Interventional Cardiology (1990-2011).

INTRODUCTION AND OBJECTIVES: The Working Group on Cardiac Catheterization and Interventional Cardiology presents a yearly report on the data collected for the national registry. This information shows how procedures are distributed throughout Spain and makes comparisons with other countries feasible. METHODS: Institutions provided their data voluntarily (online) and were analyzed by the Working Group's Steering Committee. RESULTS: Data were provided by 108 hospitals (72 public and 36 private) that mainly treat adults, Covering 138,480 diagnostic procedures, 123,746 of which were coronary angiograms, slightly more than the year before, with a rate of 3008 coronary angiograms per million population. Percutaneous coronary interventions decreased slightly to 63,202 procedures with a rate of 1373 interventions per million population. Of the 94,701 stents implanted, 61% were drug-eluting stents. In the acute phase of myocardial infarction, 15,491 coronary interventions were performed, 9.4% more than in 2010, representing 24.6% of the total number of coronary interventions. The most frequent intervention for adult congenital heart disease was atrial septal defect closure (298 procedures). Percutaneous mitral valvuloplasty continued to decrease (286 procedures) and percutaneous aortic valve implantations increased, but at a slower pace than in the previous year, with 770 units implanted in 2011. CONCLUSIONS: The greatest increase in activity has occurred in the field of myocardial infarction and percutaneous aortic valve implantation. The number of other procedures, both diagnostic and therapeutic, remained stable.

Double antiplatelet therapy after drug-eluting stent implantation: risk associated with discontinuation within the first year.

OBJECTIVES: The goal of this study was to assess the risk associated with double antiplatelet therapy (DAT) discontinuation, and specifically, temporary discontinuation, during the first year after drug-eluting stent (DES) implantation. BACKGROUND: Doubts remain about the risk of temporary DAT discontinuation within 1 year after DES implantation. METHODS: A total of 1,622 consecutive patients undergoing DES implantation at 29 hospitals were followed up at 3, 6, 9, and 12 months to record the 1-year antiplatelet therapy discontinuation (ATD) rate, the number of days without DAT, and the rate of 1-year major cardiac events. Cox regression was used to analyze the association between ATD considered as a time-dependent covariate and 1-year cardiac events. RESULTS: One hundred seventy-two (10.6%) patients interrupted at least 1 antiplatelet drug during the first year after DES implantation, although only 1 during the first month. Most (n=111, 64.5%) interrupted DAT temporarily (median: 7 days; range: 5 to 8.5): 79 clopidogrel (31 temporarily), 38 aspirin (27 temporarily), and 55 both drugs (53 temporarily). Discontinuation was followed by acute coronary syndrome in 7 (4.1%; 95% confidence interval [CI]: 1.7 to 8.2), a similar rate of major cardiac events to that in patients without ATD (n=80; 5.5%; 95% CI: 4.4 to 6.8; p=0.23). ATD was not independently associated with 1-year major cardiac events (hazard ratio: 1.32 [95% CI: 0.56 to 3.12]). CONCLUSIONS: ATD within the first year and beyond the first month after DES is not exceptional, is usually temporary, and does not appear to have a large impact on risk.

[Spanish cardiac catheterization and coronary intervention registry. 20th official report of the spanish society of cardiology working group on cardiac catheterization and interventional cardiology (1990-2010)]. / Registro Español de Hemodinámica y Cardiología Intervencionista. XX Informe Oficial de la Sección de Hemodinámica y Cardiología Intervencionista de la Sociedad Española de Cardiología (1990-2010).

INTRODUCTION AND OBJECTIVES: The Working Group on Cardiac Catheterization and Interventional Cardiology presents on a yearly basis a report on the data collected for the national registry. This information displays how procedures are distributed throughout Spain and makes comparisons with other countries feasible. METHODS: Institutions render their data voluntarily (online) and they are analyzed by the Working Group's steering committee. RESULTS: Data was sent by 113 hospitals (71 public and 41 private) that treat mainly adults, reporting 135 486 diagnostic procedures, 119 118 of them coronary angiograms, slightly less than the year before, and with a rate of 2945 coronary angiograms per million inhabitants. Percutaneous coronary interventions increased a bit, to 64331 procedures and a rate of 1398 interventions per million. Of 100371 stents implanted, 61.3% were drug-eluting stents. In the acute phase of myocardial infarction, 14248 coronary interventions were carried out, 6% more than in 2009 and 22% of the total number of coronary interventions. The most frequent intervention for adult congenital heart disease was closure of an atrial septal defect (295 procedures). Percutaneous mitral valvuloplasty continues to decrease (326 procedures) and percutaneous aortic valve implantations are growing rapidly, with 655 units implanted in 2010. CONCLUSIONS: The greatest increase in activity has occurred in the field of myocardial infarction and percutaneous aortic valve implantation. The other procedures, both diagnostic and therapeutic, remain stable.

Primary percutaneous coronary intervention for ST-segment elevation acute myocardial infarction in nonagenarian patients: results from a Spanish multicentre registry.

AIMS: Data on primary percutaneous coronary intervention for ST-segment elevation in nonagenarian patients are very limited. Our aim was to evaluate the results of primary percutaneous coronary intervention in patients ≥ 90 years old with ST-segment elevation acute myocardial infarction. METHODS AND RESULTS: We conducted a multicentre registry focused on nonagenarians treated with percutaneous coronary interventions, gathering data from five tertiary centres in Spain. We included 38 patients with ST-segment elevation acute myocardial infarction who presented within 12 hours after symptoms onset and who were treated with primary percutaneous intervention. Mean age was 91.5 (90-98). Angiographic success was achieved in 90%, and TIMI 3 flow in 76% of cases. In-hospital mortality was 34.2%, concentrated in patients with major bleeding (100% vs. 31.4%), final TIMI flow grade <3 (71.4% vs. 22.7%), and Killip class > I at admission (53.3% vs. 21.7%). CONCLUSIONS: Primary percutaneous coronary intervention in nonagenarians with ST-segment elevation acute myocardial infarction is associated with high rate of successful recanalisation of the infarct-related artery. Mortality is concentrated in patients with severe bleeding during hospitalisation, heart failure at admission, and final TIMI flow <3.

Spanish Cardiac Catheterization and Coronary Intervention Registry. 19th Official Report of the Spanish Society of Cardiology Working Group on Cardiac Catheterization and Interventional Cardiology (1990-2009).

INTRODUCTION AND OBJECTIVES: Each year the Spanish Society of Cardiology Working Group on Cardiac Catheterization and Interventional Cardiology reports on the data collected by the national registry of procedures performed. This report covers 2009. It contains information on the implementation of interventional cardiology across Spain and enables comparisons to be made with other countries. METHODS: Data were provided voluntarily and were analyzed by the Working Group's steering committee. RESULTS: Data were submitted by 126 hospitals that mainly performed procedures in adults: 74 public and 52 private. Overall, 137,166 diagnostic procedures were carried out, including 122,961 coronary angiograms; the rate of 2664 coronary angiograms per million population was little changed from the previous year. The number of percutaneous coronary interventions increased by 2% to reach 63,075, which corresponds to 1391 per million population. In total, 102,850 stents were implanted (58.7% drug-eluting). In addition, 13,395 interventions were carried out during the acute phase of myocardial infarctions: this represents a 10% increase relative to 2008 and accounts for 21% of all percutaneous coronary interventions. The most frequent intervention for adult congenital heart disease was closure of an atrial septal defect, with 329 procedures. The most frequently performed valve procedure was mitral valvuloplasty, with 336 cases treated (success rate 96%), with the exception of percutaneous aortic valve implantation, which increased exponentially to a total of 426 in 2009. CONCLUSIONS: The most significant increases in activity were in procedures for ST-segment elevation acute myocardial infarction and in percutaneous valve implantation. There was only a modest increase in the use of all other diagnostic and therapeutic procedures.

Background, incidence, and predictors of antiplatelet therapy discontinuation during the first year after drug-eluting stent implantation.

BACKGROUND: Predictors of antiplatelet therapy discontinuation (ATD) during the first year after drug-eluting stent implantation are poorly known. METHODS AND RESULTS: This was a prospective study with 3-, 6-, 9-, and 12-month follow-up of patients receiving at least 1 drug-eluting stent between January and April 2008 in 29 hospitals. Individual- and hospital-level predictors of ATD were assessed by hierarchical-multinomial regression analysis. ATD could be assessed in 1622 candidates for follow-up (82.5%). A total of 234 patients (14.4%) interrupted at least 1 antiplatelet therapy drug, predominantly clopidogrel (n=182, 11.8%). Bleeding events or invasive procedures led to ATD in 109 patients. This was predicted by renal impairment (odds ratio [OR] 2.81, 95% confidence interval [CI] 1.48 to 5.34), prior major hemorrhage (OR 3.77, 95% CI 1.41 to 10.03), and peripheral arterial disease (OR 1.78, 95% CI 1.01 to 3.15). Medical decisions led to ATD in 70 patients; this was predicted by long-term use of anticoagulant therapy (OR 3.88, 95% CI 1.26 to 11.98), undergoing the procedure in a private hospital (OR 13.3, 95% CI 1.69 to 105), and not receiving instructions about medication (OR 2.8, 95% CI 1.23 to 6.36). Thirty-nine patients interrupted ATD on their own initiative, mainly immigrants (OR 3.78, 95% CI 1.2 to 11.98) and consumers of psychotropic drugs (OR 2.58, 95% CI 1.3 to 5.12). CONCLUSIONS: ATD during the first year after drug-eluting stent implantation is based mainly on patient decision or a medical decision not associated with major bleeding events or major surgical procedures. Individual- and hospital-level variables are important to predict ATD.

2-Methoxy-3-methyl-6-oxo-4-(2,3,4-tri-O-acetyl-beta-D-xylopyranosylamino)-1,6-dihydropyrimidine-5-carbaldehyde 0.065-hydrate and 2-methylsulfanyl-6-oxo-4-(2,3,4-tri-O-acetyl-beta-D-xylopyranosylamino)-1,6-dihydropyrimidine-5-carbaldehyde: hydrogen-bonded structures in one or three dimensions.

The organic components of 2-methoxy-3-methyl-6-oxo-4-(2,3,4-tri-O-acetyl-beta-D-xylopyranosylamino)-1,6-dihydropyrimidine-5-carbaldehyde 0.065-hydrate, C(18)H(23)N(3)O(10).0.065H(2)O, (I), which crystallizes with Z' = 2 in the space group P2(1)2(1)2(1), are linked into a three-dimensional framework structure by a combination of four C-H...O hydrogen bonds. In 2-methylsulfanyl-6-oxo-4-(2,3,4-tri-O-acetyl-beta-D-xylopyranosylamino)-1,6-dihydropyrimidine-5-carbaldehyde, C(17)H(21)N(3)O(9)S, (II), where the pyrimidine fragment is disordered with two different conformations for the methylsulfanyl substituent, molecules are linked into chains of rings by a combination of N-H...O and C-H...O hydrogen bonds.

The use of proliferation signal inhibitors in the prevention and treatment of allograft vasculopathy in heart transplantation.

Cardiac allograft vasculopathy (CAV) currently represents one of the most important causes of long-term morbidity and mortality in the heart transplant population. In well-designed studies with de novo patients, the use of proliferation signal inhibitors (PSIs; everolimus and sirolimus) has been shown to significantly prevent the intimal growth of graft coronary arteries in comparison to other immunosuppressive regimens, reducing the incidence of vasculopathy at 12 and 24 months. In addition, conversion to PSIs in maintenance patients with established CAV has also shown promising results in the reduction of the progression of the disease and its clinical consequences. For these reasons the interest shown by various transplantation units in the potential role of PSIs in this field is growing. The aim of the present article is to review the information obtained to date on the use of PSIs in heart transplant recipients, both in the prevention and the treatment of CAV. The principal published recommendations on the introduction and appropriate management of these drugs in clinical practice are also collected, as well as certain recommendations given by the authors based on their experience.

[Comparison of drug-eluting and bare metal stents in saphenous vein grafts. Immediate and long-term results]. / Comparación de los stents liberadores de fármaco y los convencionales en puentes de safena. Resultados inmediatos y a largo plazo.

INTRODUCTION AND OBJECTIVES: Drug-eluting stents (DES) reduce the restenosis rate in native vessels. However, results in saphenous vein grafts (SVG) are less clear. The aim of this study was to compare DES and bare metal stents (BMS) in de novo stenosis in SVG. METHODS: The study included all percutaneous interventions involving a DES in SVG carried out at five centers up until July 2007. Findings were compared with those in a historical cohort that used conventional stents at two centers. The study analyzed in-hospital and long-term outcomes and predictors of survival and revascularization. RESULTS: The study included 107 stenoses treated with DESs in 98 patients and 130 stenoses treated with BMS in 113 patients. The DES group was older at baseline and had thrombus less often. There were also procedural differences: in the DES group, stents were longer, direct stenting was used less, and the stent diameter was smaller. The proportion of patients who experienced cardiac death by 12, 24 and 30 months was 95%+/-2%, 91%+/-3% and 89%+/-3%, respectively, in the DES group and 95%+/-2%, 90%+/-3% and 87%+/-3% in the BMS group (P=.66). The proportion without target vessel revascularization at 12, 24 and 30 months was 90%+/-3%, 86%+/-4% and 83%+/-4%, respectively, in the DES group and 94%+/-2%, 87%+/-3% and 87%+/-3% in the BMS group (P=.49). The only predictor of cardiac death was the ejection fraction. There was no predictor of revascularization. CONCLUSIONS: In our series, using DESs in SVGs was not associated with a reduction in mortality or target vessel revascularization. The only predictor of cardiac death was the ejection fraction. There was no predictor of revascularization.

Structural comparisons of isomeric series of 7-aryl-benzo[h]pyrazolo[3,4-b]quinolines and 11-aryl-benzo[f]pyrazolo[3,4-b]quinolines.

The structures of three new 7-aryl-benzo[h]pyrazolo[3,4-b]quinolines, 8-methyl-7-(4-chlorophenyl)-10-phenyl-6,10-dihydro-5H-benzo[h]pyrazolo[3,4-b]quinoline, C(27)H(20)ClN(3), 8-methyl-7-(3-pyridinyl)-10-phenyl-6,10-dihydro-5H-benzo[b]pyrazolo[3,4-b]quinoline, C(26)H(20)N(4), and 8-methyl-7-(4-pyridinyl)-10-phenyl-10H-benzo[h]pyrazolo[3,4-b]quinoline, C(26)H(18)N(4), which is an unexpected oxidation product isolated from the attempted synthesis of 8-methyl-7-(4-pyridinyl)-10-phenyl-6,10-dihydro-5H-benzo[h]pyrazolo[3,4-b]quinoline, and those of three new 11-aryl-benzo[f]pyrazolo[3,4-b]quinolines, 11-(4-methylphenyl)-10-methyl-8-phenyl-6,8-dihydro-5H-benzo[f]pyrazolo[3,4-b]quinoline, C(28)H(23)N(3) (P\bar 1, Z' = 2), 11-(4-methoxyphenyl)-10-methyl-8-phenyl-6,8-dihydro-5H-benzo[f]pyrazolo[3,4-b]quinoline, C(28)H(23)N(3)O (P2(1)/c, Z' = 4), and 11-(3,4,5-trimethoxyphenyl)-10-methyl-8-phenyl-6,8-dihydro-5H-benzo[f]pyrazolo[3,4-b]quinoline, C(30)H(27)N(3)O(3), are reported. The crystal structures are compared with those of a number of analogues reported in the recent literature; in particular, structural comparisons are drawn within each series as the substituted pendent aryl group is varied, and between several pairs of strictly isomeric 7-aryl-benzo[h]pyrazolo[3,4-b]quinolines and 11-aryl-benzo[f]pyrazolo[3,4-b]quinolines containing the same aryl substituents within each pair. Intermolecular interactions of the C-H...pi type are found in the crystal structures of both series, but pi...pi stacking interactions are found only in the 7-aryl-benzo[h]pyrazolo[3,4-b]quinoline series.

Redetermination of 6-amino-5-formyl-1,3-dimethyluracil monohydrate at 120 K: a polarized molecular structure and two interwoven hydrogen-bonded frameworks.

The title compound [systematic name: 6-amino-5-formyl-1,3-dimethylpyrimidine-2,4(1H,3H)-dione monohydrate], C(7)H(9)N(3)O(3).H(2)O, has been reexamined at 120 K. The improved precision of the intramolecular dimensions provides evidence for a polarized molecular-electronic structure, and the molecular components are linked by one N-H...O and two O-H...O hydrogen bonds into two interwoven three-dimensional frameworks, which are weakly linked by the longer component of a three-centre N-H...(O)(2) hydrogen bond.

3-[5-(4-Bromophenyl)-1H-pyrazol-3-ylamino]-5,5-dimethylcyclohex-2-en-1-one-(Z)-3-(4-bromophenyl)-3-chloroacrylonitrile (2/1): a stoichiometric cocrystal of a reaction product with one of its early precursors.

The title compound, 2C17H18BrN3O.C9H5BrClN, was crystallized from the reaction between 5,5-dimethylcyclohexane-1,3-dione, triethyl orthoformate and 5-amino-3-(4-bromophenyl)pyrazole, which had itself been prepared from the reaction between (Z)-3-(4-bromophenyl)-3-chloroacrylonitrile and hydrazine. The compound is a stoichiometric 2:1 cocrystal of the reaction product 3-[5-(4-bromophenyl)-1H-pyrazol-3-ylamino]-5,5-dimethylcyclohex-2-en-1-one and the early reactant (Z)-3-(4-bromophenyl)-3-chloroacrylonitrile. The two independent molecules of cyclohex-2-en-1-one are linked by N-H...N and N-H...O hydrogen bonds into complex bilayers and the molecules of acrylonitrile are trapped within large cavities in the substructure formed by the cyclohex-2-en-1-one molecules.

Three substituted (E)-3-aryl-2-(thienyl)acrylonitriles: isolated molecules, simple hydrogen-bonded chains and hydrogen-bonded sheets.

The structure of (E)-2-(2-thienyl)-3-(3,4,5-trimethoxyphenyl)acrylonitrile, C16H15NO3S, contains no direction-specific intermolecular interactions. The molecules of (E)-3-(4-bromophenyl)-2-(2-thienyl)acrylonitrile, C13H8BrNS, exhibit orientational disorder of the thienyl fragment, and the molecules are linked into simple C(5) chains by a single C-H...N hydrogen bond. In (E)-3-phenyl-2-(3-thienyl)acrylonitrile, C13H9NS, the molecules are linked into sheets by a combination of one C-H...N hydrogen bond and one C-H...pi(arene) hydrogen bond.