A Hirshfeld Surface Analysis and Crystal Structure of 2’-[1-(2-Fluoro-Phenyl)-1H-tetrazol-5-Yl]-4-Methoxy-Biphenyl-2-Carbaldehyde

Kumar, Shankar; Manjunath, B.C.; Lingaraju, Gejjalagere S.; Abdoh, Muneer; Sadashiva, M. P.; Lokanath, N.K.

doi:10.4236/csta.2013.23017

Cited by 25 publications

(9 citation statements)

References 22 publications

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“…The DSC and DTA curves indicate that the compound 7 e exhibits two endothermic peaks at 277 & 532 °C and an exothermic peak at 592 °C. The TGA curve shows that the compound started decomposition at 276 °C, which indicates the compound is free from moisture . The compound has observed a maximum weight loss between 323 and 553 °C represents the maximum rate of decomposition.…”

Section: Resultsmentioning

confidence: 97%

Synthesis, Characterization, Molecular Docking Studies and Biological Evaluation of Some Conjugated Quinazoline‐Sulfonamide Scaffold

Kumar¹,

Kudva²,

Bharath³

et al. 2018

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A series of sulfonamides containing 4-aminoquinazoline scaffolds 7 a-7 l was synthesized, characterized and evaluated for their in vitro antitubercular, antimicrobial and anticancer activity. The compounds with 4-nitrophenyl (7 c), 3-trifluoromethylphenyl (7 f) and 5-chloro-pyridin-2-yl (7 h) derivatives have shown potent antitubercular activity against Mycobacterium tuberculosis H37Rv strain and the activity was two-fold higher than the standard drug Ciprofloxacin. The compounds with 4chlorophenyl (7 a), pyridin-2-yl (7 g), 5-chloro-pyridin-2-yl (7 h) and pyrimidin-2-yl (7 i, 7 j and 7 k) derivatives were observed as excellent antimicrobial agents. The preliminary toxicity of selected potent compounds was also tested on Red Blood Cells by hemolytic assay and found to be non-toxic even at higher concentrations. Compounds with 4-nitrophenyl (7 c) and 4fluorophenyl (7 e) substitutions emerged as potent molecules against MDA-MB-231 cell line. ADME (Absorption, Distribution, Metabolism and Excretion) screening study revealed that the compounds are strong candidates for antitubercular activity with good ADME parameters. In addition, the structure and antitubercular activity relationship were further supported by molecular docking studies of the active compounds against the DNA topoisomerase II (5BTC) enzyme of M. tuberculosis.[a] A.

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Section: Resultsmentioning

confidence: 97%

Synthesis, Characterization, Molecular Docking Studies and Biological Evaluation of Some Conjugated Quinazoline‐Sulfonamide Scaffold

Kumar¹,

Kudva²,

Bharath³

et al. 2018

ChemistrySelect

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“…The intercontacts with respect to d i and d e were plotted using 2D-fingerprint plot as shown in the Figure 5 . 74 , 83 − 86 …”

Section: Experimental Sectionmentioning

confidence: 99%

Efficient Synthesis and in Silico Studies of the Benzimidazole Hybrid Scaffold with the Quinolinyloxadiazole Skeleton with Potential α-Glucosidase Inhibitory, Anticoagulant, and Antiplatelet Activities for Type-II Diabetes Mellitus Management and Treating Thrombotic Disorders

et al. 2018

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The current study evaluates antidiabetic, anticoagulant, and antiplatelet activity of novel benzimidazole-containing quinolinyl oxadiazoles. These derivatives are synthesized and characterized using spectroscopy (FT-IR, 1H NMR, and mass spectroscopy) and single-crystal X-ray diffraction methods. The inhibitory effects of these compounds were evaluated by the α-glucosidase inhibitory assay and shows the activity in the range of IC50 = 0.66 ± 0.05 to 3.79 ± 0.46 μg/mL. In addition, molecular docking studies revealed that benzimidazole-containing quinolinyl oxadiazoles can correctly dock into the target receptor protein of the human intestinal α-glucosidase, while their bioavailability/drug-likeness was predicted to be acceptable but requires further optimization. On the other hand, compound 8a and 8d showed anticoagulant activity as they enhanced the clotting time from control 180–410 and 180–390 s, respectively, in platelet rich plasma and 230–460 and 230–545 s in platelet poor plasma. Furthermore, only 8a showed antiplatelet activity by inhibiting epinephrine-induced platelet aggregation, and the observed aggregation inhibition was found to be 93.4%. Compounds 8a–f show nontoxic properties because of the non-hydrolyzing properties in the RBC cells. In addition, 8a and 8d show anti-edema and anti-hemorrhagic properties in the experimental mice. These findings reveal that benzimidazole-containing quinolinyl oxadiazoles act as α-glucosidase inhibitors to develop novel therapeutics for treating type-II diabetes mellitus and can act as lead molecules in drug discovery as potential antidiabetic and antithrombotic agents.

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“…5 illustrates the distribution of positive and negative potential over the Hirshfeld surfaces. Blue regions correspond to positive electrostatic potential (indicating hydrogen-bond donors) and the red regions to negative electrostatic potential (indicating hydrogen-bond acceptors) (Kumar et al, 2013).…”

Section: Hirshfeld Surface Analysismentioning

confidence: 99%

Crystal structure of 2,3-dimethoxy-N-(4-nitrophenyl)benzamide

et al. 2018

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In the title compound, C15H14N2O5, the benzene rings are nearly coplanar, making a dihedral angle of 4.89 (8)°. An intramolecular N—H...O hydrogen bond occurs between the imino and methoxy groups. In the crystal, weak C—H...O hydrogen bonds link the molecules into supramolecular chains propagating along thea-axis direction. π–π stacking is observed between parallel benzene rings of neighbouring chains, the centroid-to-centroid distance being 3.6491 (10) Å. Three-dimensional Hirshfeld surface analyses and two-dimensional fingerprint plots have been used to analyse the intermolecular interactions present in the crystal.

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A Hirshfeld Surface Analysis and Crystal Structure of 2’-[1-(2-Fluoro-Phenyl)-1H-tetrazol-5-Yl]-4-Methoxy-Biphenyl-2-Carbaldehyde

Cited by 25 publications

References 22 publications

Synthesis, Characterization, Molecular Docking Studies and Biological Evaluation of Some Conjugated Quinazoline‐Sulfonamide Scaffold

Synthesis, Characterization, Molecular Docking Studies and Biological Evaluation of Some Conjugated Quinazoline‐Sulfonamide Scaffold

Efficient Synthesis and in Silico Studies of the Benzimidazole Hybrid Scaffold with the Quinolinyloxadiazole Skeleton with Potential α-Glucosidase Inhibitory, Anticoagulant, and Antiplatelet Activities for Type-II Diabetes Mellitus Management and Treating Thrombotic Disorders

Crystal structure of 2,3-dimethoxy-N-(4-nitrophenyl)benzamide

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