One pot Click chemistry: A three component reaction for the synthesis of 2-mercaptobenzimidazole linked coumarinyl triazoles as anti-tubercular agents

Anand, Ashish; Kulkarni, Manohar V.; Joshi, Shrinivas D.; Dixit, Sheshagiri R.

doi:10.1016/j.bmcl.2016.08.045

Cited by 49 publications

(20 citation statements)

References 22 publications

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“…The process is mediated by a Click type reaction between 2-propargylthiobenzimidazole (85), 4-bromomethyl coumarins/1-aza-coumarins 86 and sodium azide, in the presence of CuSO 4 /sodium ascorbate as catalytic system (Scheme 36). The anti-tubercular assays of the obtained compounds 87 against M. tuberculosis (H37Rv) coupled with in silico molecular docking studies indicated that dimethyl substituted products 87c (X = O, R = 5,7-diMe) and 87d (X = O, R = 7,8-diMe) showed promising activity with higher C-score values [84]. The products were evaluated against Mycobacterium tuberculosis H37Rv (MTB) and cytotoxicity.…”

Section: Anti-mycobacterial Activitymentioning

confidence: 99%

Synthesis of Biologically Active Molecules through Multicomponent Reactions

et al. 2020

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Focusing on the literature progress since 2002, the present review explores the highly significant role that multicomponent reactions (MCRs) have played as a very important tool for expedite synthesis of a vast number of organic molecules, but also, highlights the fact that many of such molecules are biologically active or at least have been submitted to any biological screen. The selected papers covered in this review must meet two mandatory requirements: (1) the reported products should be obtained via a multicomponent reaction; (2) the reported products should be biologically actives or at least tested for any biological property. Given the diversity of synthetic approaches utilized in MCRs, the highly diverse nature of the biological activities evaluated for the synthesized compounds, and considering their huge structural variability, much of the reported data are organized into concise schemes and tables to facilitate comparison, and to underscore the key points of this review.Molecules 2020, 25, 505 2 of 71 acetylcholinesterase inhibitors, anti-HIV, antimicrobial, antioxidant, anti-mycobacterial and anticancer activities ( Figure 1). It is noteworthy that 64% and 16% of the supporting literature found for this review correspond to heterocyclic structures with anticancer and antimicrobial activities, respectively. Scheme 2. Three-component synthesis of 3,4-dihydropyrimidinones/thiones type 7 under microwave irradiation, for anti-inflammatory activity.Patil et al., reported a one-pot pseudo-five-component synthesis of highly functionalized tetrahydropyridines 9 using Cu(OTf) 2 as catalyst, Scheme 3. In vitro anti-inflammatory activity of the obtained compounds 9 was determined against matrix metalloproteinases (MMPs) as MMP-2 and MMP-9 by using gelatin zymography [29]. Scheme 3. Multicomponent Cu(OTf) 2 catalyzed synthesis of substituted tetrahydropyridines 9 for anti-inflammatory activity.A highly diastereoselective synthesis (exclusively the cis isomer is formed), of chromeno β-lactam hybrids 13/14 was also achieved by an efficient one-pot three-component reaction between either 5,5-dimethylcyclohexane-1,3-dione (10a) or 4-hydroxycoumarin (10b), diverse benzaldehydes 11 and malononitrile (12), in the presence of DABCO under reflux conditions (Scheme 4). Scheme 4. Three-component synthesis of β-lactam hybrids 13/14 for anti-inflammatory activity.The synthesized compounds (13 in 80-95% yield) and (14 in 82-95% yield) were screened for anti-inflammatory activity (as well as for anticancer activity, please see Section 3.13.13. Compound 13b (Ar = 4-ClC 6 H 4 , Ar 1 = 4-MeC 6 H 4 ) was the most active of all the chromeno β-lactam hybrids 13/14 tested, with a 19.8 anti-inflammatory ratio, although, it resulted less active than the reference drug dexamethasone corticosteroid used for the treatment of rheumatoid and skin inflammation [30].

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Section: Anti-mycobacterial Activitymentioning

confidence: 99%

Synthesis of Biologically Active Molecules through Multicomponent Reactions

et al. 2020

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“…As a result, 37 (Figure ) was effective against M. tuberculosis H37Rv ATCC 27294 with an MIC value of 0.5 μg/ml. In particular, Compound 37 showed an MIC value of 0.125–0.5 μg/ml against four kinds of TB clinical isolate (Anand, Kulkarni, Joshi, & Dixit, ; Zhang et al, ).…”

Section: Five‐membered Ring Compoundsmentioning

confidence: 99%

“…Kulkarni and his colleagues designed and synthesized a set of 1,4‐disubstituted triazoles in one pot under Click chemistry conditions. Compounds 47a and 47b (Figure ) displayed potent anti‐TB activities against MTB H37Rv with an MIC value of 3.8 μM (Anand et al, ; Zhang et al, ).…”

Section: Five‐membered Ring Compoundsmentioning

confidence: 99%

Opportunities and challenges of using five‐membered ring compounds as promising antitubercular agents

Wang

et al. 2020

Drug Development Research

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Tuberculosis (TB), a chronic infectious disease, is one of the greatest risks to human beings and 10 million people were diagnosed with TB and 1.6 million died from this disease in 2017. In addition, with the emergence of multidrug-resistant tuberculosis (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB), the TB situation has become even worse, which has aggravated the mortality and spread of this disease.To overcome this problem, research into novel antituberculosis agents with enhanced activities against MDR-TB, reduced toxicity, and shortened duration of therapy is of great importance. Fortunately, many novel potential anti-TB drug candidates with five-membered rings, which are most likely to be effective against sensitive and resistant strains, have recently entered clinical trials. Different five-membered rings such as furans, pyranoses, thiazoles, pyrazolines, imidazoles, oxazolidinone, thiazolidins, isoxazoles, triazoles, oxadiazoles, thiadiazoles, and tetrazoles have been designed, prepared, and evaluated for their antimycobacterial activity against Mycobacterium tuberculosis. In this article, we highlight the recent advances made in the discovery of novel five-membered ring compounds and focus on their antitubercular activities, toxicity, structure-activity relationships, and mechanisms of action. K E Y W O R D Santi-TB drug, antitubercular activities, five-membered ring, MDR-TB, tuberculosis

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“…The compounds derived from 2-mercaptobenzimidazole have attracted the attention of several researchers for their properties which exhibit significant biological and pharmacological activities such as antibacterial, antioxidant [1][2][3] , anticonvulsant 4 , antimicrobial 5 antihistaminic 6 nootropic 7 , anti-tubercular 8 and analgesic 9 activities. Although, a great interest of the scientific literature concerning 2-mercaptobenzimidazole is in the area of medicinal chemistry, 2-mercaptobenzimidazole is also used in non-biological applications, it serves as plant growth regulators 10 , as natural rubber 11 and used as corrosion inhibitor for mild steel [12][13][14][15][16] .…”

Section: Introductionmentioning

confidence: 99%

Novel 2-mercaptobenzimidazole derivatives: synthesis and evaluation of its antibacterial and antioxidant activities

Ouasif

Bouyahya

Zniber³

et al. 2017

Mediterr.J.Chem.,

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In the present study, a series of novel 2-mercapto-benzimidazolium were synthesized from 2-mercapto-benzimidazole with hydrocarbon chains. All compounds obtained are reported for the first time, and the structures of these compounds were confirmed by means of 1H-NMR, 13C-NMR and mass spectrometry. The newly synthesized compounds were subjected to in vitro biological evaluation. The antibacterial activity was evaluated will diffusion assay and density optic method. The antioxidant activity was carried out using DPPH free radical scavenging assay. The result indicated that some compounds show convincing antibacterial activities against two microorganisms: Escherichia coli and Staphylococcus aureus. While, these molecules have not shown interesting antioxidant effects.

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One pot Click chemistry: A three component reaction for the synthesis of 2-mercaptobenzimidazole linked coumarinyl triazoles as anti-tubercular agents

Cited by 49 publications

References 22 publications

Synthesis of Biologically Active Molecules through Multicomponent Reactions

Synthesis of Biologically Active Molecules through Multicomponent Reactions

Opportunities and challenges of using five‐membered ring compounds as promising antitubercular agents

Novel 2-mercaptobenzimidazole derivatives: synthesis and evaluation of its antibacterial and antioxidant activities

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