Author
Wei He
Bio: Wei He is an academic researcher from Nanjing Tech University. The author has contributed to research in topics: Isopropyl & Hydrogen bond. The author has an hindex of 2, co-authored 2 publications receiving 24 citations.
Topics: Isopropyl, Hydrogen bond, Pyran, Carboxylate, Dihedral angle
Papers
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TL;DR: In this paper, the title compound, C21H16FNO3·CH3OH, was synthesized by the reaction of 1-naphthol with methyl cyanoacetate and 3-fluoro-benzaldehyde in methanol under microwave irradiation.
Abstract: The title compound, C21H16FNO3·CH3OH, was synthesized by the reaction of 1-naphthol with methyl cyanoacetate and 3-fluorobenzaldehyde in methanol under microwave irradiation. The pyran rings of the two independent molecules in the asymmetric unit adopt boat conformations. The crystal packing is stabilized by intermolecular N—H⋯O, O—H⋯O and C—H⋯π interactions.
21 citations
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TL;DR: In the title compound, C16H18FN3O2, the benzene and pyrimidine rings are oriented at a dihedral angle of 55.92°.
Abstract: In the title compound, C16H18FN3O2, the benzene and pyrimidine rings are oriented at a dihedral angle of 55.92 (2)°. In the crystal structure, intermolecular N—H⋯N and C—H⋯F hydrogen bonds are found.
3 citations
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TL;DR: 4H-chromenes 8h and 8i exhibit promising anti-cancer properties and can be used as lead compounds for further development and evaluation of Lipinski and ADMET properties revealed their drug-like pharmacokinetic profiles.
Abstract: A series of N-methyl-3-nitro-4-(nitromethyl)-4H-chromen-2-amine derivatives 8 were synthesized from 2-((E)-2-nitrovinyl)phenol 7 and ((E)-N-methyl)-1-(methylthio)-2-nitroethenamine 5. The cytotoxic activity of these molecules was tested against two cancer cell lines namely HeLa (cervical cancer) and HEp-2 (epidermoid laryngeal carcinoma). Among them, two molecules (4H-chromenes 8h and 8i) displayed potent anti-proliferative activity with IC50 values of 115.04 and 18.96 μM for HeLa and 86.94 and 25.08 μM for Hep-2 cell lines, respectively. Morphological evaluation of the cell lines revealed that both 8h and 8i induce the apoptotic process. Molecular docking studies of all the 4H-chromenes 8 with anti-apoptotic Bcl-2, Bcl-w, and Bcl-xL proteins revealed that the 4H-chromenes 8h and 8i have good docking score and thus corroborated in vitro studies. Furthermore, evaluation of Lipinski and ADMET properties revealed their drug-like pharmacokinetic profiles. Thus, 4H-chromenes 8h and 8i exhibit promising anti-cancer properties and can be used as lead compounds for further development.
22 citations
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TL;DR: The findings show that the C4-malononitrile and C2-N-phenyl-substituted 4H-chromene are the most promising lead molecules for treatment of cancer.
Abstract: A combinatorial library of eighteen C4-active methine-substituted 4H-chromenes were synthesized, and their anti-cancer properties were evaluated against four human cancer cell lines, namely laryngeal carcinoma (Hep2), lung adenocarcinoma (A549), colon carcinoma (HT-29) and cervical cancer (HeLa). Out of them, six displayed significant anti-proliferative activity. The best among them, the 4H-chromene with C4-malononitrile substitution, was selected for further structure–activity relationship studies. Six analogues were synthesized and subjected to in vitro studies on above four cancer cell lines. The best among them was subjected to detail in silico studies by binding with Bcl-2 protein, and the results corroborated those obtained from in vitro studies. Our findings show that the C4-malononitrile and C2-N-phenyl-substituted 4H-chromene are the most promising lead molecules for treatment of cancer.
17 citations
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TL;DR: The title molecule, C21H18O8, crystallizes in two crystal polymorphs, see also Nallasivam, Nethaji, Vembu & Jaswant [Acta Cryst. (2009), E65, o314–o315].
Abstract: The title molecule, C21H18O8, crystallizes in two crystal polymorphs, see also Nallasivam, Nethaji, Vembu & Jaswant [Acta Cryst. (2009), E65, o314–o315]. The molecules of both polymorphs differ by the conformation of the oxomethylacetate groups. The title molecules are rather planar compared to the molecules of the other polymorph. In the title molecule, one of the oxomethylacetate groups is disordered (occupancies of 0.6058/0.3942). The structures of both polymorphs are stabilized by C—H⋯O and C—H⋯π interactions. Due to the planarity of the title molecules and similar intermolecular interactions, the title molecules are more densely packed than those of the other polymorph.
4 citations
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TL;DR: In the title compound, C29H23N3O4, the 2-methylpyrrolidine ring adopts a twist conformation on the N—C bond involving the spiro C atom, while the hydropyran ring adopTS an envelope conformation with the methine C atom bonded to the O atom as the flap.
Abstract: In the title compound, C29H23N3O4, the 2-methylpyrrolidine ring adopts a twist conformation on the N—C bond involving the spiro C atom, while the hydropyran ring adopts an envelope conformation with the methine C atom bonded to the O atom as the flap. The mean plane of the indoline-2-one ring system is almost perpendicular to the mean plane of the pyrrolidine ring, making a dihedral angle of 89.73 (8)°. The latter ring makes dihedral angles of 47.80 (8) with the naphthalene ring system and 32.38 (8)° with the hydropyran ring mean plane. There is an intramolecular C-H⋯O hydrogen bond involving the indoline-2-one O atom. In the crystal, adjacent molecules are linked via N—H⋯O hydrogen bonds, forming chains propagating along [100]. The chains are linked via weak C—H⋯O hydrogen bonds, forming two-dimensional networks, lying parallel to (101), and consolidated by C—H⋯π interactions.
3 citations
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TL;DR: In the title compound, C11H9Cl2N3O5, the dihydropyran ring adopts a near-half-chair conformation and the molecular structure displays an S(6) motif formed by intramolecular N—H⋯O hydrogen bonding.
Abstract: In the title compound, C11H9Cl2N3O5, the dihydropyran ring adopts a near-half-chair conformation. The benzene ring makes a torsion angle of 5.02 (5)° with the dihydropyran ring. Adjacent molecules are interlinked through intermolecular C—H⋯O, N—H⋯O and C—Cl⋯π [3.4743 (9) A] interactions. The intermolecular N—H⋯O hydrogen bond generates an R 2 2(12) motif, which is observed to contribute to the crystal packing stability. Moreover, the molecular structure displays an S(6) motif formed by intramolecular N—H⋯O hydrogen bonding.
3 citations