Enhanced Method for the Synthesis and Comprehensive Characterization of 1-(4-Phenylquinolin-2-yl)propan-1-one.

We present an enhanced method for synthesizing a novel compound, 1-(4-phenylquinolin-2-yl)propan-1-one (3), through the solvent-free Friedländer quinoline synthesis using poly(phosphoric acid) as an assisting agent. The crystal structure of compound 3 is analyzed using FT-IR, and the chemical shifts of its 1H- and 13C NMR spectra are measured and calculated using B3LYP/6-311G(d,p), CAM-B3LYP/6-311G(d,p), and M06-2X/6-311G(d,p) basis sets in the gas phase. Additionally, the optimized geometry of quinoline 3 is compared with experimental X-ray diffraction values. Through density functional theory calculations, we explore various aspects of the compound's properties, including noncovalent interactions, Hirshfeld surface analysis, nonlinear optical properties, thermodynamic properties, molecular electrostatic potential, and frontier molecular orbitals. These investigations reveal chemically active sites within this quinoline derivative that contribute to its chemical reactivity.

Design and synthesis of novel pyrrolo[2,3-a]carbazoles: 7-Chloro-2-oxo-3a-(2'-oxo-2',3'-dihydro-1'H-indol-3'-yl)-2,3,3a,4,5,10-hexahydro-pyrrolo[3,2-a]carbazole-1-carbonitrile as an efficient anticancer agent.

Highly efficient poly functionalized pyrrolo[3,2-a]carbazoles via ring contraction through rearrangement and intramolecular Michael addition reaction using one pot multicomponent reaction (MCR) is reported for the first time. Free radical scavenging and anticancer activities were determined by DPPH and MTT assays respectively. Of these, compound 8d exhibited most potent activity against HCT-15 human colon cancer cell lines with an IC50 value of 9.9 µM and low toxicity toward normal human red blood cells. The morphological changes were visualized using scanning electron microscopy (SEM) technique, intracellular ROS generation measured by spectrofluorometer and gene expression levels of caspase-3, caspase-9 and Bcl-2 were determined using Semi quantitates PCR analysis for the target compound. Further, the structure activity relationships were also carried out. The results of the present study revealed that among pyrrolo[3,2-a]carbazole compounds, 7-chloro-2-oxo-3a-(2'-oxo-2',3'-dihydro-1'H-indol-3'-yl)-2,3,3a,4,5,10-hexahydro-pyrrolo[3,2-a]carbazole-1-carbonitrile could be exploited as an excellent anticancer agent against colon cancer cells.

Regio- and stereoselective synthesis of dispirooxindole-pyrrolocarbazole hybrids via 1,3-dipolar cycloaddition reactions: Cytotoxic activity and SAR studies.

A library of novel dispiro compounds containing oxindole-pyrrolo-carbazole hybrid frame works has been synthesized in a fully regio- and stereoselective fashion by the three-component 1,3-dipolar cycloaddition of azomethineylides generated in situ from the condensation of isatins and benzylamine with 2-arylidene/heteroarylidene-2,3,4,9-tetrahydro-1H-carbazole-1-one. The structures of the compounds were established by FT-IR, 1H NMR, 13C NMR, X-ray diffraction and elemental analysis. The synthesized dispiro heterocycles have been screened for in vitro cytotoxic activity by MTT assay and displayed enviable growth inhibition on both the cancer cell lines i.e. breast cancer cell line MCF-7 and lung cancer cell line A-549. Morphological changes and apoptosis induction have been studied by inverted light microscopic, fluorescent microscopic techniques and by flow cytometry analyses. The preliminary structure activity relationships were also carried out. Data indicated that among dispiro-carbazole compounds,6-chloro-4'-(thiophen-2-yl)-5'-phenyl-3,4-dihydrodispiro[carbazole-2,3'-pyrrolo-2',3″-indole]-9(H)-1,2″-dione 7e could be exploited as a significant therapeutic drug against breast cancer as well as lung cancer cell proliferation.

Synthesis of hetero annulated isoxazolo-, pyrido- and pyrimido carbazoles: Screened for in vitro antitumor activity and structure activity relationships, a novel 2-amino-4-(3'-bromo-4'-methoxyphenyl)-8-chloro-11H-pyrimido[4,5-a]carbazole as an antitumor agent.

Claisen-Schmidt condensation of 2,3,4,9-tetrahydro-1H-carbazol-1-one with 3-bromo-4-methoxy benzaldehyde afforded the 2-(3'-bromo-4'-methoxybenzylidene)-2,3,4,9-tetrahydro-1H-carbazol-1-one 3. Compound 3 was allowed to react with different organic reactants, hydroxylamine hydrochloride, malononitrile and guanidine nitrate through condensation cum cycloaddition reactions to afford a series of the respective novel hetero annulated carbazoles such as isoxazolo-, pyrido- and pyrimido carbazoles. The structures of the compounds were established by FT-IR, 1H NMR, 13C NMR, X-ray diffraction and elemental analysis. The compounds have been screened for in vitro anti-tumor activity by MTT assay and displayed enviable selective growth inhibition on MCF-7 cell line compared to A-549 cell line. Apoptotic morphological changes in MCF-7 and A-549 cells were visualized using fluorescent microscopic technique. The preliminary structure activity relationships were also carried out. Data pointed out that among pyrimido carbazole compounds, 2-amino-4-(3'-bromo-4'-methoxyphenyl)-8-chloro-11H-pyrimido [4,5-a]carbazole could be exploited as an excellent therapeutic drug against cancer cell proliferation.

Synthesis, antimicrobial, antimycobacterial and structure-activity relationship of substituted pyrazolo-, isoxazolo-, pyrimido- and mercaptopyrimidocyclohepta[b]indoles.

A new class of heterocycles, specifically substituted pyrazolo-, isoxazolo- and pyrimidocyclohepta[b]indoles, has been prepared by condensation of substituted 7-(hydroxymethylene)-7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-ones with hydrazine hydrate, hydroxylamine hydrochloride, phenylhydrazine, urea and thiourea, respectively. The structures of the compounds were established by IR, (1)H NMR, (13)C NMR, mass spectral analysis, X-ray diffraction, and the compounds have been screened for in vitro antimicrobial and antimycobacterial against Mycobacterium tuberculosis H37Rv (MTB). Among the compounds screened, five substances were found to have an MIC of 3.12 µg/ml or greater against MTB. Structure-activity relationship (SAR) analyses and in silico drug relevant properties (HBD, HBA, PSA, c Log P, M.wt) confirmed that the compounds are potential lead compounds for future drug discovery studies.