Synthesis, crystal studies, anti-tuberculosis and cytotoxic studies of 1-[(2E)-3-phenylprop-2-enoyl]-1H-benzimidazole derivatives

Kalalbandi, Veerendra Kumar A.; Seetharamappa, J.; Katrahalli, Umesha; Bhat, Kishore

doi:10.1016/j.ejmech.2014.04.017

Cited by 38 publications

(25 citation statements)

References 30 publications

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“…The most important result of our work was the achievement of a derivative with the same activity as a first line drug. Compound 8 presented a MIC value of 6.25 μg·mL −1 , the same value as found for streptomycin [32]. This is an important result, since it is the same activity as that presented by a first line drug currently in use for anti-tuberculosis treatment (see Table 2).…”

Section: Resultssupporting

confidence: 63%

New Non-Toxic Semi-Synthetic Derivatives from Natural Diterpenes Displaying Anti-Tuberculosis Activity

et al. 2015

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Abstract:We report herein the synthesis of six diterpene derivatives, three of which are new, generated through known organic chemistry reactions that allowed structural modification of the existing natural products kaurenoic acid (1) and copalic acid (2). The new compounds were fully characterized using high resolution mass spectrometry, infrared spectroscopy, 1 H-and 13 C-NMR experiments. We also report the evaluation of the anti-tuberculosis potential for all compounds, which showed some promising results for Micobacterium tuberculosis inhibition. Moreover, the toxicity for each of the most active compounds was also assessed.

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Section: Resultssupporting

confidence: 63%

New Non-Toxic Semi-Synthetic Derivatives from Natural Diterpenes Displaying Anti-Tuberculosis Activity

et al. 2015

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“…Benzimidazole is a popular nucleus in structural manipulation in medicinal chemistry and has been intensively discussed in the literature [ 19 , 21 , 22 , 23 , 24 ] and many benzimidazoles are reported to show anthelmintic [ 25 , 26 ], antimicrobial [ 27 , 28 , 29 , 30 , 31 , 32 ], anti-HIV [ 33 , 34 , 35 ], antiviral [ 36 , 37 ], anti-inflammatory [ 38 , 39 ], anticancer [ 40 , 41 , 42 , 43 , 44 ], anticonvulsant [ 45 ], antidiabetic [ 45 , 46 ], antihypertensive [ 47 ], anti-tuberculosis [ 48 , 49 ], antimalarial [ 50 , 51 ] and antioxidant [ 52 , 53 ] activities.…”

Section: Benzazolesmentioning

confidence: 99%

Importance of Fluorine in Benzazole Compounds

2020

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Fluorine-containing heterocycles continue to receive considerable attention due to their unique properties. In medicinal chemistry, the incorporation of fluorine in small molecules imparts a significant enhancement their biological activities compared to non-fluorinated molecules. In this short review, we will highlight the importance of incorporating fluorine as a basic appendage in benzothiazole and benzimidazole skeletons. The chemistry and pharmacological activities of heterocycles containing fluorine during the past years are compiled and discussed.

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“…For that, designing drugs for the treatment of tuberculosis has been a challenging area in medicinal chemistry in view of the multi-drug resistance [79] and high mortality rate [80] associated with this disease. Among the approved anti-tubercular drugs, benzimidazole derivatives appear as privileged and promising structures in chemotherapy of tuberculosis [81][82][83]. As a contribution to this topic, Anand et al, reported a three-component reaction for the synthesis of 2-mercaptobenzimidazole linked coumarinyl triazoles 87 as anti-tubercular agents.…”

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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Synthesis, crystal studies, anti-tuberculosis and cytotoxic studies of 1-[(2E)-3-phenylprop-2-enoyl]-1H-benzimidazole derivatives

Cited by 38 publications

References 30 publications

New Non-Toxic Semi-Synthetic Derivatives from Natural Diterpenes Displaying Anti-Tuberculosis Activity

New Non-Toxic Semi-Synthetic Derivatives from Natural Diterpenes Displaying Anti-Tuberculosis Activity

Importance of Fluorine in Benzazole Compounds

Synthesis of Biologically Active Molecules through Multicomponent Reactions

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