A highly atom economic, chemo-, regio- and stereoselective synthesis and evaluation of spiro-pyrrolothiazoles as antitubercular agents

Karthikeyan, Subramanian Vedhanarayanan; Bala, Balasubramanian Devi; Raja, V. P. Alex; Perumal, S.; Yogeeswari, Perumal; Sriram, Dharmarajan

doi:10.1016/j.bmcl.2009.10.107

Cited by 99 publications

(36 citation statements)

References 35 publications

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“…Synthesis of heterocyclic compounds having both thiazolone and spirooxindole moieties via 1,3-dipolar cycloaddition reaction of azomethine ylides generated in situ by the decarboxylative condensation of isatin with 1,3-thiazolane-4-carboxylic acid 135 with dipolarophiles such as 180, 80 216, 81 and 82 82 has been reported (Scheme 62). …”

Section: Synthesis Of Dispiropyrrolothiazolo-oxindolesmentioning

confidence: 99%

Synthesis of heterocyclic compounds based on isatin through 1,3-dipolar cycloaddition reactions

Lashgari¹,

Ziarani²

2012

Arkivoc

136

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Section: Synthesis Of Dispiropyrrolothiazolo-oxindolesmentioning

confidence: 99%

Synthesis of heterocyclic compounds based on isatin through 1,3-dipolar cycloaddition reactions

Lashgari¹,

Ziarani²

2012

Arkivoc

136

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“…Kartikeyan et al. synthesized a series of novel spiro‐pyrrolothiazoles and compound 234 showed more potency (MIC = 0.6 μM) than ethambutol (MIC = 7.6 μM) and pyrazinamide (MIC = 50.8 μM) against M. tuberculosis H37Rv . In another report, compound 235 was reported to be the most potent of all synthesized derivatives by exhibiting MICs of 1.76 and 0.88 μM against M. tuberculosis H37Rv and MDR‐TB, respectively (Fig.…”

Section: Pyrrolidines and Pyrrolizinesmentioning

confidence: 99%

“…In another report, a series of novel spiro-pyrido-pyrrolizines and pyrrolidines were synthesized and compound 233 exhibited MIC value of 0.4 mg/mL against M. tuberculosis H37Rv, while against MDR-TB strain, it displayed fourfold more potency compared to first-line drug isoniazid (MIC = 1.56 g/mL) 199. Kartikeyan et al synthesized a series of novel spiro-pyrrolothiazoles and compound 234 showed more potency (MIC = 0.6 M) than ethambutol (MIC = 7.6 M) and pyrazinamide (MIC = 50.8 M) against M. tuberculosis H37Rv 200. In another report, compound 235 was reported to be the most potent of all synthesized derivatives by exhibiting MICs of 1.76 and 0.88 M against M. tuberculosis H37Rv and MDR-TB, respectively (Fig.…”

mentioning

confidence: 99%

New structural classes of antituberculosis agents

Kumar

Patel

Jain

2017

Medicinal Research Reviews

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Tuberculosis (TB), one of the deadliest diseases is shattering the health and socioeconomic status of the society. The emergence of multidrug resistant (MDR) and extremely drug resistant (XDR) strains has provided unprecedented lethal character to TB. The development of MDR and XDR strains of TB results in more deaths, longer duration of therapy, and appearance of the disease in the immunocompromised patients. Because of the development of rapid resistance by Mycobacterium tuberculosis, researchers are confronted with serious challenges in combating TB. For instance, the need for potency and specificity in therapeutic agents approaching clinics, and the increasing demand of low toxicity due to long duration of treatment. Recently, it is proposed that such challenges could be addressed by a shift from contemporary or known classes of drugs to new scaffold-containing or entirely new structural classes of drugs that possibly act on the previously unknown targets, resulting in possibly less instances of resistance development. The exploitation of advances made in the biology of TB in the last and present decades have created opportunities to discover a large number of new structural classes that specifically targets TB by molecular mechanism of action(s) unknown earlier. We have earlier reviewed new structural classes of anti-TB agents up to year 2005. This review covers literature reports of the subsequent 10 years on the discovery of new structural classes of synthetic anti-TB agents. Due to the availability of large number of research reports, we have divided new compounds in 38 structural classes, 368 structures, and 307 references.

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“…Finally, they found that the activity of the compound depends on the nature of the substituent groups (electron withdrawing) with the following sequence NO 2 > Cl > Br > OCH 3 < OH > CH 3 (Samdhiya et al, 2010). On the other hand, hybridization of Spiro compound and pyrrolo2,1-b thiazole, an unusual ring with different biological properties, particularly permitted the obtention of pyrrolothiazoles derivatives (44, figure 13) that present a MIC of 0.007 µM against M. tuberculosis, being more potent than INH and Ciprofloxacin (Karthikeyan et al, 2010) . Fig.…”

Section: Azoles Derivativesmentioning

confidence: 99%

Antitubercular Drugs Development: Recent Advances in Selected Therapeutic Targets and Rational Drug Design

Bocanegra-García¹,

García²,

Palma-Nicolás³

et al. 2011

Drug Development - A Case Study Based Insight Into Modern Strategies

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A highly atom economic, chemo-, regio- and stereoselective synthesis and evaluation of spiro-pyrrolothiazoles as antitubercular agents

Cited by 99 publications

References 35 publications

Synthesis of heterocyclic compounds based on isatin through 1,3-dipolar cycloaddition reactions

Synthesis of heterocyclic compounds based on isatin through 1,3-dipolar cycloaddition reactions

New structural classes of antituberculosis agents

Antitubercular Drugs Development: Recent Advances in Selected Therapeutic Targets and Rational Drug Design

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