Design of novel dispirooxindolopyrrolidine and dispirooxindolopyrrolothiazole derivatives as potential antitubercular agents

Mhiri, Chourouk; Boudriga, Sarra; Askri, Moheddine; Knorr, Michael; Sriram, Dharmarajan; Yogeeswari, Perumal; Nana, Frédéric; Golz, Christopher; Strohmann, Carsten

doi:10.1016/j.bmcl.2015.07.069

Cited by 39 publications

(19 citation statements)

References 52 publications

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“…synthesized a series of novel dispirooxindolopyrrolidines and dispirooxindolopyrrolothiazoles and evaluated their activity against M. tuberculosis . Two analogues 229 and 230 exhibited identical MIC value of 1.56 μg/mL that was similar to standard drug ethambutol (MIC = 1.56 μg/mL) . After an investigation against growing and nongrowing M. tuberculosis , pyrrolidine dithiocarbamate derivative 231 exhibited MIC value of 0.13 μg/mL, and synergic effect with pyrazinamide and rifampin .…”

Section: Pyrrolidines and Pyrrolizinesmentioning

confidence: 89%

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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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Section: Pyrrolidines and Pyrrolizinesmentioning

confidence: 89%

“…187 was similar to standard drug ethambutol (MIC = 1.56 g/mL). 196 After an investigation against growing and nongrowing M. tuberculosis, pyrrolidine dithiocarbamate derivative 231 exhibited MIC value of 0.13 g/mL, and synergic effect with pyrazinamide and rifampin. 197 Fig.…”

Section: -mentioning

confidence: 99%

New structural classes of antituberculosis agents

Kumar

Patel

Jain

2017

Medicinal Research Reviews

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“…According to the literature, isoniazide could bind with NAD + and block the oxidation–reduction reaction to inhibit Mtb growth (Mhiri et al, ). The introduction of a pyrazole ring into the INH analogues might improve the activity of the novel compounds against susceptible and resistant TB strains.…”

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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“…investigated the in vitro anti‐TB activity of spiroisatins 49 (Fig. ) against MTB H37Rv and MDR‐TB, and the preliminary results indicated that all the synthetic spiroisatins showed great potency against MTB H37Rv with MIC in a range of 0.6 to 49.2 μM, which were more potent than PZA (MIC: 50.2 μM) . The most active spiroisatins 49a–f (MIC: 0.6–2.8 μM) were further evaluated for their in vitro activities against MDR‐TB, and all of them were more active than the first‐line anti‐TB agents RIF , INH , EMB , and PZA (MIC: 3.8, 11.4, 61.2, and 406.1 μM) .…”

Section: Spiroisatin Derivativesmentioning

confidence: 99%

Isatin Derivatives with Potential Antitubercular Activities

Jiang

Wang

Liu

et al. 2018

Journal of Heterocyclic Chem

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Tuberculosis is a life‐threatening chronic infectious disease, which primarily affects the lungs but can spread to other vital organs. The re‐emergence and wide spread of new virulent forms of Mycobacterium tuberculosis that are resistant to some or all first and second line antitubercular agents has reached an alarming level in recent decades. Thus, it is imperative to develop more effective agents. Isatin derivatives are endowed with diverse biological properties, therefore thousands of isatin derivatives have been synthesized in hopes of discovering new candidates with potential antitubercular activities against both drug‐susceptible and drug‐resistant strains. This review summarizes the recent developments of isatin derivatives with potential antitubercular activities.

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Design of novel dispirooxindolopyrrolidine and dispirooxindolopyrrolothiazole derivatives as potential antitubercular agents

Cited by 39 publications

References 52 publications

New structural classes of antituberculosis agents

New structural classes of antituberculosis agents

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

Isatin Derivatives with Potential Antitubercular Activities

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