Synthesis andin vitroantimicrobial activity of novelN-(6-chlorobenzo[d]thiazol-2-yl) hydrazine carboxamide derivatives of benzothiazole class

Gilani, Sadaf Jamal; Khan, Samia; Siddiqui, Nadeem; Verma, Sonia; Mullick, Pooja; Alam, Ozair

doi:10.3109/14756366.2010.508441

Cited by 21 publications

(10 citation statements)

References 26 publications

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“…The compounds α- and β-amyrin are triterpenes of natural origin, commonly detected in various plant materials, such as steam bark residues of Byrsonima crassifolia (9 g/kg) [46] and leaves of Byrsonima fagifolia (2.3 g/Kg) [47,48,49]. Therapeutic effects of these substances have been confirmed by subsequent in vitro and in vivo assays for various diseases, such as inflammation, microbial, fungal, and viral infections, and cancer cells [50]. In the literature, hydrazine carboxamide was documented as an antimicrobial agent that inhibits the growth of some bacterial strains, such as Staphylococcus aureus, Klebsiella pneumoniae, Escherichia coli, Pseudomonas aeruginosa, and some fungal species, such as Aspergillus niger, Aspergillus flavus, Penicillium citrinum, Candida albicans, and Monascus purpereus [49].…”

Section: Discussionmentioning

confidence: 99%

“…In the literature, hydrazine carboxamide was documented as an antimicrobial agent that inhibits the growth of some bacterial strains, such as Staphylococcus aureus, Klebsiella pneumoniae, Escherichia coli, Pseudomonas aeruginosa, and some fungal species, such as Aspergillus niger, Aspergillus flavus, Penicillium citrinum, Candida albicans, and Monascus purpereus [49]. Recently, this compound was found to greatly contribute to arresting the growth of lung cancer cells of Eclipta alba [50]. Fucosterol belongs to phytosterol identified in seaweed brown algae, which has been shown to be active as an antidiabetic, antiosteoporotic, and antioxidant [51,52].…”

Section: Discussionmentioning

confidence: 99%

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Comprehensive Fractionation of Antioxidants and GC-MS and ESI-MS Fingerprints of Celastrus hindsii Leaves

et al. 2019

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Background: In this study, column chromatography was applied to separate active fractions from the ethyl acetate extract of Celastrus hindsii, a medicinal plant widely used in Southern China, Northern Vietnam, Myanmar, and Malaysia. Methods: Fourteen fractions from different dilutions of chloroform and methanol were separated by column chromatography and examined for biological activities. Results: It was found that a dilution of 50–70% methanol in chloroform yielded the highest total phenolics, flavonoids, and antioxidant activities (1,1-dipheny1-2-picrylhydrazyl (DPPH), 2,2-azinobis (3-ehtylbenzothiazoline-6-sulfonic acid), diammonium salt (ABTS) radical scavenging activity, and β-carotene bleaching method measured by lipid peroxidation inhibition). In addition, by gas chromatography-mass spectrometry (GC-MS) and electrospray ionization-mass spectrometry (ESI-MS) analyses, fifteen principal compounds from bioactive fractions belonging to fatty acids, amides, flavonoids, sterols, terpenes, and phenols were identified. Of these compounds, α-amyrin, β-amyrin, hydrazine carboxamide, hexadecanoic acid, fucosterol, (3β)-D:C-friedours-7-en-3-ol, rutin, and 2-hydroxy-1-ethyl ester accounted for maximal quantities, whilst concentrations of other constituents were <5%. Conclusions: It is suggested that these identified compounds may greatly contribute to the antioxidant capacity of C. hindsii as well as its potential pharmaceutical properties.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Comprehensive Fractionation of Antioxidants and GC-MS and ESI-MS Fingerprints of Celastrus hindsii Leaves

et al. 2019

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“…Compounds 6-chlorobenzothiazol-2-amine 3 [49], 6-fluorobenzothiazol-2-amine 4 [50], 2-amino-5-chlorobenzenethiol 5 [51], 2-amino-5-fluorobenzenethiol 6 [52], 27a [53], 27b [54], 27c [55], 28a [54], 28b [54], 28c [54], 29a [55], 29b [54], 29c [54], 30a [54], 30b [28], 30c [28], 31a [25], 31b [54], 31c [54], 32 [29], 33 [30], hydrochloride 38a [28], hydrochloride 38b [28], hydrochloride 39c [28], hydrochloride 40a [28], hydrochloride 40b [28], hydrochloride 40c [28], hydrochloride 41a [28], hydrochloride 41c [28], were synthesized in accordance with procedures given in the literature.…”

Section: Experimental Procedures For Preparation Of Compoundsmentioning

confidence: 99%

Synthesis, Antiproliferative Evaluation and QSAR Analysis of Novel Halogen- and Amidino-Substituted Benzothiazoles and Benzimidazoles

Kaulić

Racané

Leventić

et al. 2022

IJMS

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Syntheses of 6-halogen-substituted benzothiazoles were performed by condensation of 4-hydroxybenzaldehydes and 2-aminotiophenoles and subsequent O-alkylation with appropriate halides, whereas 6-amidino-substituted benzothiazoles were synthesized by condensation of 5-amidino-2-aminothiophenoles and corresponding benzaldehydes. While most of the compounds from non-substituted and halogen-substituted benzothiazole series showed marginal antiproliferative activity on tested tumor cell lines, amidino benzazoles exhibited stronger inhibitory activity. Generally, imidazolyl benzothiazoles showed pronounced and nonselective activity, with the exception of 36c which had a strong inhibitory effect on HuT78 cells (IC50 = 1.6 µM) without adverse cytotoxicity on normal BJ cells (IC50 >100 µM). Compared to benzothiazoles, benzimidazole structural analogs 45a–45c and 46c containing the 1,2,3-triazole ring exhibited pronounced and selective antiproliferative activity against HuT78 cells with IC50 < 10 µM. Moreover, compounds 45c and 46c containing the methoxy group at the phenoxy unit were not toxic to normal BJ cells. Of all the tested compounds, benzimidazole 45a with the unsubstituted phenoxy central core showed the most pronounced cell growth inhibition on THP1 cells in the nanomolar range (IC50 = 0.8 µM; SI = 70). QSAR models of antiproliferative activity for benzazoles on T-cell lymphoma (HuT78) and non-tumor MDCK-1 cells elucidated the effects of the substituents at position 6 of benzazoles, demonstrating their dependence on the topological and spatial distribution of atomic mass, polarizability, and van der Waals volumes. A notable cell cycle perturbation with higher accumulation of cells in the G2/M phase, and a significant cell increase in subG0/G1 phase were found in HuT78 cells treated with 36c, 42c, 45a–45c and 46c. Apoptotic morphological changes, an externalization of phosphatidylserine, and changes in the mitochondrial membrane potential of treated cells were observed as well.

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“…Hydrazides, hydrazonoyl halides and hydrazonoyl cyanides exhibit a wide spectrum of biological activities including antimicrobial [ 1 , 2 , 3 , 4 , 5 , 6 , 7 ], antifungal [ 8 , 9 ], antibacterial [ 8 , 10 ], antituberculotic [ 5 , 11 ], anticancer, anti-inflammatory and analgesic effects [ 12 ]. The biological activities and applications of hydrazone derivatives were comprehensively reviewed by Rollas and Küçükgüzel [ 13 ], Kumar and Narasimhan [ 14 ] and Narang et al [ 15 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Herbicidal Activity of New Hydrazide and Hydrazonoyl Derivatives

et al. 2015

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Three new hydrazide and five new hydrazonoyl derivatives were synthesized. The chemical structures of these compounds were confirmed by 1H-NMR, IR spectroscopy and elemental analysis. The prepared compounds were tested for their activity to inhibit photosynthetic electron transport in spinach chloroplasts and growth of the green algae Chlorella vulgaris. IC50 values of these compounds varied in wide range, from a strong to no inhibitory effect. EPR spectroscopy showed that the active compounds interfered with intermediates Z•/D•, which are localized on the donor side of photosystem II. Fluorescence spectroscopy suggested that the mechanism of inhibitory action of the prepared compounds possibly involves interactions with aromatic amino acids present in photosynthetic proteins.

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Synthesis andin vitroantimicrobial activity of novelN-(6-chlorobenzo[d]thiazol-2-yl) hydrazine carboxamide derivatives of benzothiazole class

Cited by 21 publications

References 26 publications

Comprehensive Fractionation of Antioxidants and GC-MS and ESI-MS Fingerprints of Celastrus hindsii Leaves

Comprehensive Fractionation of Antioxidants and GC-MS and ESI-MS Fingerprints of Celastrus hindsii Leaves

Synthesis, Antiproliferative Evaluation and QSAR Analysis of Novel Halogen- and Amidino-Substituted Benzothiazoles and Benzimidazoles

Synthesis and Herbicidal Activity of New Hydrazide and Hydrazonoyl Derivatives

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