An efficient new method of ytterbium(III) triflate catalysis approach to the synthesis of substituted pyrroles: DFT, ADMET, and molecular docking investigations.

In this study, the one-pot synthetic methodology for the preparation of substituted pyrroles with diethyl acetylene-dicarboxylate is reported for the various pyrrole derivatives via the Trifimow synthesis process from oximes. This method also offers the literature as a cyclization pathway using a ytterbium triflate catalyst. Another importance of this study is the use of pyrrole derivatives in pharmaceuticals, biological processes, and agrochemicals. From this point of view, the development of a new catalyst in synthetic organic chemistry and the difference in the method is also important. The syntheses of the target substituted pyrroles are accomplished in high yields. Also, all synthesized structures were confirmed by 1H NMR, 13C NMR, and IR spectra. The DFT computations were leveraged for structural and spectroscopic validation of the compounds. Then, FMO and NBO analyses were subsequently employed to elucidate the reactivity characteristics and intramolecular interactions within these compounds. Also, ADMET indices were ascertained to assess potential pharmacokinetic properties, drug-like qualities, and possible adverse effects of these compounds. Last, optimized molecules were analyzed by molecular docking methods against crystal structures of Bovine Serum Albumin and Leukemia Inhibitory Factor, and their binding affinities, interaction details, and inhibition constants were determined.

Strychnos alkaloids: total synthesis, characterization, DFT investigations, and molecular docking with AChE, BuChE, and HSA.

An efficient five steps, the protection-deprotection synthetic a novel synthetic routes to(±) noruleine (±)-uleine, are reported starting from tetrahydrocarbazole fused monoalkyl nitrile at C-2 position that is prepared on multigram scale from 2-(3-ethyl-1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetonitrile (1) as well as the key azocino[4,3-b]indole skeleton is constructed via the tetrafluoro-1,4-benzoquinone (TFB)-mediated cyclization of a tetrahydrocarbazole derivative possessing direct amide synthesis from nitrile. As a result, Total synthesis of noruleine and uleine has been developed, which is accomplished in 4 and 5- steps synthesis of the ABCD tetracyclic of the strychnos alkaloids with an overall yield of 44% and 39%, respectively. The DFT computations were performed with B3LYP/6-311g(d,p) level to determine inter and intramolecular interactions and reactivity features of the compound 3-6. Also, TD-DFT computations were performed to characterize the electronic absorption spectra of all compounds. Last, the interactions of compounds 3-6 with selected targets AChE, BuChE, and HSA were evaluated in light of the molecular dockings. The bioactivity and drug-likeness scores revealed that compound 6 3-6 can be proper candidate for future drug-design studies more than the other compounds.

New route for synthesis of 2-(2,2-dimethoxyethyl)-1,2,3,4,5,6-hexahydro-1,5-methanoazocino[4,3-b]indole and DFT investigation.

Development of efficient sequences for the synthesis of the title compound (2-(2,2-dimethoxyethyl)-1,2,3,4,5,6-hexahydro-1,5-methanoazocino[4,3-b]indole) (7) was described. The title compound was synthesized through several steps starting from phenylhydrazine hydrochloride and dimethyl (R)-2-(3-oxocyclohexyl)malonate. In this route, all synthesized compounds were observed by spectroscopic tools (FT-IR, NMR): Methyl-2-(2,3,4,9-1H-carbazol-2-yl)acetate (3), 2-(2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetic acid (4), N-(2,2-dimethoxyethyl)-2-(2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetamide (5), 2-(2,2-dimethoxyethyl)-1,2,4,5,6,7-hexahydro-3H-1,5-methanoazocino[4,3-b]indol-3-one (6), 2-(2,2-dimethoxyethyl)-2,3,4,5,6,7-hexahydro-1H-1,5-methanoazocino[4,3-b]indole (7). The central step in these syntheses is the dehydrogenative reaction, which constructs the tetracyclic ring system from a much simpler tetracyclic precursor. The six-stable conformers of the compound (7) were used for further calculations such as FT-IR, NMR, NLO, and FMO analyses, performed at the B3LYP/6-311++G(d,p) level. This work revealed that (7) can be a good material to use in the non-linear optical material because its ß tensor is greater ten times than that of the urea.

9H-Carbazole-9-carbo-thioic di-thio-peroxy-anhydride.

The whole mol-ecule of the title compound, C26H16N2S4, is generated by twofold rotational symmetry. The carbazole skeleton is nearly planar [maximum deviation = 0.054 (5) Å]. In the crystal, aromatic π-π stacking is observed between parallel carbazole ring systems of adjacent mol-ecules, the shortest centroid-centroid distances between pyrrole and benzene rings being 3.948 (3) and 3.751 (3) Å.

9-(4-Nitro-phenyl-sulfon-yl)-9H-carbazole.

In the title mol-ecule, C(18)H(12)N(2)O(4)S, the carbazole skeleton is nearly planar [maximum deviation = 0.037 (1) Å] and is oriented at a dihedral angle of 73.73 (5)° with respect to the benzene ring. An intra-molecular C-H⋯O hydrogen bond links a nitro O atom to the carbazole skeleton. In the crystal, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network. π-π contacts between inversion-related benzene rings [centroid-centroid distance = 3.7828 (8) Å] and two weak C-H⋯π inter-actions may also stabilize the structure.

5-(3,6-Dibromo-9H-carbazol-9-yl)penta-nenitrile.

In the title compound, C(17)H(14)Br(2)N(2), the carbazole skeleton is nearly planar [maximum deviation = 0.055 (2) Å]. In the crystal, aromatic π-π stacking is observed between parallel carbazole ring systems of adjacent mol-ecules, the shortest centroid-centroid distance between benzene rings being 3.4769 (11) Å.

9-Benzyl-9H-carbazole.

The asymmetric unit of the title compound, C(19)H(15)N, contains two crystallographically independent mol-ecules. In both mol-ecules, the planar carbazole moieties [maximum deviations = 0.037 (4) and 0.042 (3) Å] are oriented with respect to the adjacent benzene rings, at dihedral angles of 85.29 (8) and 89.89 (7)°, respectively. In the crystal structure, weak C-H⋯π inter-actions are observed involving the carbazole rings.

3,3-Ethyl-enedithio-3,3a,4,5,10,10b-hexa-hydro-2H-furo[2,3-a]carbazole.

The title compound, C(16)H(17)NOS(2), consists of a carbazole skeleton with tetra-hydro-furan and dithiol-ane rings. In the indole ring system, the benzene and pyrrole rings are nearly coplanar, forming a dihedral angle of 1.57 (15)°. The cyclo-hexenone and tetra-hydro-furan rings have envelope conformations, while the dithiol-ane ring adopts a twist conformation. In the crystal structure, pairs of weak inter-molecular N-H⋯S hydrogen bonds link the mol-ecules into centrosymmetric dimers with R(2) (2)(16) ring motifs. Weak C-H⋯π inter-actions may further stabilize the structure.