Crystal structure of (E)-2-fluorobenzaldehyde (pyridin-2-yl)hydrazone

The title compound, C12H10FN3, is approximately planar: the dihedral angles between the mean plane of the central N—N=C spacer unit and the fluorobenzene and pyridine rings are 14.50 (13) and 4.85 (15)°, respectively, while the dihedral angle between the aromatic rings is 16.29 (6)°. The F atom lies at the same side of the molecule as the N atom of the pyridine ring. In the crystal, inversion dimers linked by pairs of N—H...N hydrogen bonds generate R22(8) loops. Molecules related by translation in the a direction are linked by two π–π stacking interactions involving pairs of benzene rings and pairs of pyridine rings. In each case, the ring-centroid separation is 3.8517 (9) Å. Two chains of this type pass through each unit cell, but there are no direction-specific interactions between adjacent chains

Crystal structures of five (2-chloro-quinolin-3-yl)methyl ethers : supra-molecular assembly in one and two dimensions mediated by hydrogen bonding and π-π stacking

In the mol­ecules of the title compounds, methyl 5-bromo-2-[(2-chloro­quinolin-3-yl)meth­oxy]benzoate, C18H13BrClNO3, (I), methyl 5-bromo-2-[(2-chloro-6-methyl­quinolin-3-yl)meth­oxy]benzoate, C19H15BrClNO3, (II), methyl 2-[(2-chloro-6-methyl­quinolin-3-yl)meth­oxy]benzoate, C19H16ClNO3, (III), which crystallizes with Z' = 4 in space group P212121, and 2-chloro-3-[(naphthalen-1-yl­oxy)meth­yl]quinoline, C20H14ClNO, (IV), the non-H atoms are nearly coplanar, but in {5-[(2-chloro­quinolin-3-yl)meth­oxy]-4-(hy­droxy­meth­yl)-6-methyl­pyridin-3-yl}methanol, C18H17ClN2O3, (V), the planes of the quinoline unit and of the unfused pyridine ring are almost parallel, although not coplanar. The mol­ecules of (I) are linked by two independent [pi]-[pi] stacking inter­actions to form chains, but there are no hydrogen bonds present in the structure. In (II), the mol­ecules are weakly linked into chains by a single type of [pi]-[pi] stacking inter­action. In (III), three of the four independent mol­ecules are linked by [pi]-[pi] stacking inter­actions but the other mol­ecule does not participate in such inter­actions. Weak C-H...O hydrogen bonds link the mol­ecules into three types of chains, two of which contain just one type of independent mol­ecule while the third type of chain contains two types of mol­ecule. The mol­ecules of (IV) are linked into chains by a C-H...π(arene) hydrogen bond, but [pi]-[pi] stacking inter­actions are absent. In (V), there is an intra­molecular O-H...O hydrogen bond, and mol­ecules are linked into sheets by a combination of O-H...N hydrogen bonds and π-π stacking inter­actions.Publisher PDFPeer reviewe

Synthesis, molecular docking, antimycobacterial and antimicrobial evaluation of new pyrrolo3,2-c]pyridine Mannich bases

In this report, we describe the synthesis and biological evaluation of a new series of pyrrolo3,2-c]pyridine Mannich bases (7a-v). The Mannich bases were obtained in good yields by one-pot three component condensation of pyrrolo3,2-c]pyridine scaffold (6a-c) with secondary amines and excess of formaldehyde solution in AcOH. The chemical structures of the compounds were characterized by H-1 NMR, C-13 NMR, LC/MS and elemental analysis. Single crystal X-ray diffraction has been recorded for compound 7k (C23H29ClN4](+2), H2O). The in vitro antimicrobial activities of the compounds were evaluated against various bacterial and fungal strains using Agar diffusion method and Broth micro dilution method. Compounds 7e, 7f, 7r, 7t, and 7u were showed good Gram-positive antibacterial activity against S. aureus, B. flexus, C sporogenes and S. mutans. Furthermore, in vitro antimycobacterial activity was evaluated against Mycobacterium tuberculosis H37Rv (ATCC 27294) using MABA. Compounds 7r, 7t, and 7u were showed good antitubercular activity against Mtb (MIC >= 6.25 g/mL). Among the tested compounds, 14(4-chloro-2-(cyclohexylmethyl)-1H-pyrrolo3,2-clpyridin-3-yl)methyl) piperidine-3-carboxamide (7t) was showed excellent antimycobacterial activity against Mtb (MIC <0.78 mu g/mL) and low cytotoxicity against the HEK-293T cell line (SI 25). Molecular docking of the active compounds against glutamate racemase (Murl) and Mtb glutamine synthetase were explained the structure-activity observed in vitro. (C) 2017 Elsevier Masson SAS. All rights reserved