Synthesis and evaluation of some new benzothiazole derivatives as potential antimicrobial agents

Soni, Balram; Ranawat, Mahendra Singh; Sharma, Rakesh; Bhandari, Anil; Sharma, Sanjay K.

doi:10.1016/j.ejmech.2010.03.019

Cited by 98 publications

(49 citation statements)

References 17 publications

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“…Benzothiazoles are a class of bicyclic compounds with a broad spectrum of biological applications such as neuroprotective effects [1,2], antimicrobial activity [3][4][5][6], antioxidant and radioprotective effects [7], anticonvulsant activity [8,9] and antitumor properties [10,11]. In particular, 2-(4-hydroxy-3-methoxyphenyl)-benzothiazole has been reported to be a tyrosinase inhibitor against hyperpigmentation [12].…”

Section: Introductionmentioning

confidence: 99%

Helical Arrangement of 2-(4-hydroxy-3-methoxyphenyl)-Benzothiazole in Crystal Formation and Biological Evaluation on HeLa Cells

et al. 2017

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Abstract:Benzothiazoles are a set of molecules with a broad spectrum of biological applications. In particular, 2-(4-hydroxy-3-methoxyphenyl)-benzothiazole is a potential breast cancer cell suppressor whose mechanism of action has been previously reported. In the present work, the title compound was synthesized, crystallized, and its biological activity on HeLa cells was evaluated. Its molecular structure was compared to that obtained by molecular modeling. Theoretical calculations suggest that the syn-rotamer is the most stable form and correlates very well with crystallographic data. The crystal structure adopts a helical arrangement formed through O13-H13···N3 intermolecular hydrogen bonding that propagates in the (14 -1 -3) plane. These results suggest that the title compound has the capacity to interleave into DNA and better explain its biological effects related to the increased CHIP expression through AhR recruitment. Finally, the biological experiments indicate that the title compound has the capacity to decrease the viability of HeLa cells with an IC 50 = 2.86 µM.

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Section: Introductionmentioning

confidence: 99%

Helical Arrangement of 2-(4-hydroxy-3-methoxyphenyl)-Benzothiazole in Crystal Formation and Biological Evaluation on HeLa Cells

et al. 2017

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Section: Introductionmentioning

confidence: 99%

“…Its favorable bioactivity has prompted widespread studies on benzothiazole derivatives in the past two decades. For example, a number of benzothiazole derivatives are shown to have antitumor, 6) antimicrobial, 7) antifungal, 8) anthelmintic, 9) anti-in ammatory, 10) cardiovascular 11) and antitubercular 12) activities.It is also reported that hydrazones possess a diverse range of bioactivities in the medicinal and agrochemical elds, such as anticancer, 13) anti-in ammatory, 14) antimicrobial, 15) herbicidal, 16) fungicidal 17) and insecticidal 18) activities. In addition, hydrazones are very useful starting materials in many reactions in the synthesis of various bioactive molecules.…”

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confidence: 99%

Synthesis and fungicidal activity of hydrazones containing 4-methylbenzo[d]thiazole moiety

2012

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A new series of hydrazone derivatives containing 4-methylbenzo [d]thiazole moiety was synthesized. e structures of the title compounds were characterized by 1 H NMR, FTIR, MS and elemental analysis. Fungicidal activities of the title compounds were investigated. e results indicated that some of these compounds exhibit excellent fungicidal activities. © Pesticide Science Society of Japan Keywords: hydrazone, benzothiazole, synthesis, fungicidal activity. IntroductionSulfur-and nitrogen-linked heterocyclic compounds have received considerable attention in recent years because of their pharmacological and pesticidal importance. [1][2][3][4][5] Benzothiazole is one of the oldest and potent heterocyclic compounds displaying interesting medicinal and agricultural activities. Its favorable bioactivity has prompted widespread studies on benzothiazole derivatives in the past two decades. For example, a number of benzothiazole derivatives are shown to have antitumor, 6) antimicrobial, 7) antifungal, 8) anthelmintic, 9) anti-in ammatory, 10) cardiovascular 11) and antitubercular 12) activities.It is also reported that hydrazones possess a diverse range of bioactivities in the medicinal and agrochemical elds, such as anticancer, 13) anti-in ammatory, 14) antimicrobial, 15) herbicidal, 16) fungicidal 17) and insecticidal 18) activities. In addition, hydrazones are very useful starting materials in many reactions in the synthesis of various bioactive molecules. 19) It is well-known that tricyclazole, a triazolo [3,4-b]benzothiazole derivative, is applied mainly as a commercial fungicide to control Pyricularia oryzae. 13) In line with our continuous e orts to synthesize bioactive lead compounds for crop protection, the title compounds were designed by introducing a hydrazone pharmacophore into the benzothiazole sca old. Our original strategy is depicted in Fig. 1. Materials and Methods InstrumentsMelting points were determined using an X-4 apparatus without calibration. 1 H NMR spectra were measured on a Bruker ADVANCE III instrument (500 MHz) using TMS as an internal standard and deuterochloroform as a solvent. FT-IR spectra were recorded on a NICOLET 6700 instrument. Mass spectra were recorded on a ermo Scienti c ITQ 1100TM and erm LCQ TM Deca XP plus instrument. Elemental analyses were performed on a Vario EL elemental analyzer. Synthesis of compoundsAll starting materials were used as purchased or of analytic grade purity. Analytical TLC was performed on silica gel GF254. e title compounds were synthesized according to the route shown in Fig. 2. 2-Hydrazino-4-methylbenzo [d]thiazole was prepared according to the reference. 20) o-Toluidine (0.2 mol) was added to water and warmed with dilute hydrochloric acid (10 mL) until a clear solution was obtained. Ammonium thiocyanate (0.22 mol) dissolved in water (50 mL), then added this solution gradually. e reaction mixture boiled at 100-110°C for 8 hr and evaporated to less than half the volume. It was then cooled to get the precipitate of compound 2, which was ltered, washed wit...

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“…The investigation and application of this strategy have prepared several interesting 1,2,4-triazole-based compounds bearing both amino and thiol groups [145]. This type of synthetic method provides practical access to amino triazole thiols which may favorably react with 1,3,4-thiadiazoles or 1,3,4-thiadiazines to prepare new types of fused heterocyclic compounds with broad bioactive spectrum such as antimicrobial [146][147][148][149], anti-inflammatory, analgesic [150,151] as well as antiepileptic activity [152].…”

Section: Thiol Thio Hydrazidesmentioning

confidence: 99%

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Zhang¹,

Damu²,

Cai³

et al. 2014

COC

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Heterocyclic 1,2,4-triazole derivatives possess unusually spacious potentiality as medicinal agents, agricultural chemicals, functional materials, ionic liquids, supramolecular catalysts as well as artificial enzymes and receptors for supramolecular recognition and biomimetic catalysis, and their various researches and developments have been being a quite rapidly developing and active highlight topic with an infinite space. Numerous efforts have been directed toward various types of possible applications of 1,2,4-triazole-based compounds and a lot of important progress has been made, especially their preparations have attracted increasing attention. This review systematically summarized the recent advances in the syntheses of 1,2,4-triazole derivatives, including: (1) Cyclizations to form triazole ring; (2) Transformations of heterocyclic compounds to construct triazole ring; (3) Substitutions on 1,2,4-triazole ring; (4) Structural modifications in side chains of 1,2,4-triazole ring. It was hoped that this review would be helpful for the design and development of highly efficient preparation of 1,2,4-triazole derivatives with various sorts and varieties of extensively potential applications in medicine, agriculture, chemistry, materials, supramolecular sciences and so on.

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Synthesis and evaluation of some new benzothiazole derivatives as potential antimicrobial agents

Cited by 98 publications

References 17 publications

Helical Arrangement of 2-(4-hydroxy-3-methoxyphenyl)-Benzothiazole in Crystal Formation and Biological Evaluation on HeLa Cells

Helical Arrangement of 2-(4-hydroxy-3-methoxyphenyl)-Benzothiazole in Crystal Formation and Biological Evaluation on HeLa Cells

Synthesis and fungicidal activity of hydrazones containing 4-methylbenzo[d]thiazole moiety

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

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