Guanidinyl benzothiazole derivatives: Synthesis and structure activity relationship studies of a novel series of potential antimicrobial and antioxidants

Bhat, Mahesh; Belagali, S. L.

doi:10.1007/s11164-016-2454-6

Cited by 31 publications

(17 citation statements)

References 32 publications

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“…From the structural activity relationship, we can summarize that electron-donating group present at para-position of substituted phenyl group and meta-substitution enhance activity. Benzothiazole guanidinyl derivatives show excellent microbial activity, as explained by Bhat et al [9], which we can correlate with the present study, as in both cases electron-donating substituted compounds showed enhanced activity (Table 3).…”

Section: Antimicrobial Activitysupporting

confidence: 92%

“…This heterocyclic scaffold is readily substituted at the unique methylene center of the thiazole ring. Based on the above facts and in continuation of our drug development program [9][10][11], in this work we synthesized amide derivatives of benzothiazole and evaluated their antimicrobial and antimitotic activities. Even though these represent different directions, we investigated both types of activity to determine the potential of these molecules.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and characterization of novel benzothiazole amide derivatives and screening as possible antimitotic and antimicrobial agents

et al. 2016

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A new series of benzothiazole amide derivatives (9a-l) were synthesized and characterized by Fourier-transform infrared (FT-IR), mass, and 1 H and 13 C nuclear magnetic resonance (NMR) spectroscopic techniques. The antimitotic activity of the newly synthesized compounds was determined by the Allium assay method, from which mitotic index values were calculated. Here, 9g (14.0 %) and 9l (14.5 %) showed mitotic index values most comparable to that of standard drug (14.4 %), while the remaining compounds showed lower mitotic index values; hence, these compounds inhibit the regular cell division process and are the most promising antimitotic agents. Based on the structural activity relationship, the maximum percentage inhibition was observed for compounds containing electron-withdrawing group, revealing enhanced antimitotic activity, while compounds with electron-donating groups such as furan (9g) and methyl (9l) were comparable to standard. The newly synthesized compounds were also screened for antimicrobial activity, with some of them showing remarkable activity.Electronic supplementary material The online version of this article (

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Section: Antimicrobial Activitysupporting

confidence: 92%

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of novel benzothiazole amide derivatives and screening as possible antimitotic and antimicrobial agents

et al. 2016

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“…Furthermore, due to efficient resonance stabilization of the charged protonated state, the guanidine groups have a relatively high acid dissociation constant which makes them stronger bases better suited for stable electrostatic interaction with the negative charged membranes of bacteria. This property improves the penetration of guanidine-bearing compounds through membranes and thus their biological activity [ 15 , 16 ]. On the other hand, the introduction of fluorine or appropriate fluorinated groups into organic compounds has advanced over recent decades in medicinal chemistry.…”

Section: Introductionmentioning

confidence: 99%

Novel Guanidine Compound against Multidrug-Resistant Cystic Fibrosis-Associated Bacterial Species

et al. 2018

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Chronic pulmonary infection is a hallmark of lung disease in cystic fibrosis (CF). Infections dominated by non-fermentative Gram-negative bacilli are particularly difficult to treat and highlight an urgent need for the development of new class of agents to combat these infections. In this work, a small library comprising thiourea and guanidine derivatives with low molecular weight was designed; these derivatives were studied as antimicrobial agents against Gram-positive, Gram-negative, and a panel of drug-resistant clinical isolates recovered from patients with CF. One novel compound, a guanidine derivative bearing adamantane-1-carbonyl and 2-bromo-4,6-difluouro-phenyl substituents (H-BDF), showed potent bactericidal activity against the strains tested, at levels generally higher than those exhibited by tobramycin, ceftazimide and meropenem. The role that different substituents exert in the antimicrobial activity has been determined, highlighting the importance of the halo-phenyl group in the guanidine moiety. The new compound displays low levels of cytotoxicity against THP-1 and A549 cells with a selective index (SI) > 8 (patent application PCT/IB2017/054870, August 2017). Taken together, our results indicate that H-BDF can be considered as a promising antimicrobial agent.

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“…They are associated with various biological activities, for example, anticancer activity , because of inhibition of vital enzymes, namely, cytochrome P450 enzyme , EGFR tyrosine kinase , or COX‐2 enzyme . In addition, these derivatives are considered as antimicrobial , anti‐inflammatory , antioxidant , antitubercular , and antimalarial agents. Moreover, incorporation of thiophene nucleus at position 2 of benzothiazole gives rise to compounds possessing potent anticancer and antimicrobial activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anticancer Evaluation of Some Novel Thiophene, Thieno[3,2‐d]pyrimidine, Thieno[3,2‐b]pyridine, and Thieno[3,2‐e][1,4]oxazepine Derivatives Containing Benzothiazole Moiety

Hassan

Husseiny

2019

Journal of Heterocyclic Chem

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In an attempt to establish novel candidate with promising anticancer activity, two derivatives of (benzo[d]thiazol‐2‐yl)thiophene backbone 1 and 14 were synthesized, and they further reacted with various chemical reagents to afford the corresponding substituted thiophene derivatives 6, 8, 10, 15, 17, and 20, thieno[3,2‐d]pyrimidine derivatives 2–5, 7, 9, 16, 21, 23, and 24, thieno[3,2‐b]pyridine derivatives 11–13, and thieno[3,2‐e][1,4]oxazepine derivative 18. Structures of prepared compounds were affirmed via spectral and elemental data. Among the obtained compounds, seven derivatives 2, 3, 4, 5, 11, 12, and 13 were chosen by National Cancer Institute, USA. Such compounds were screened for their antitumor activity versus 60 cancer cell lines in one‐dose (10 μmol) screening assay. The outcomes showed that all selected compounds exhibited moderate to high anticancer activity towards many cancer cell lines among which compounds 5 and 11 exerted potent antitumor activity against numerous malignant growth cell lines particularly Ovarian Cancer IGROV1.

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Guanidinyl benzothiazole derivatives: Synthesis and structure activity relationship studies of a novel series of potential antimicrobial and antioxidants

Cited by 31 publications

References 32 publications

Synthesis and characterization of novel benzothiazole amide derivatives and screening as possible antimitotic and antimicrobial agents

Synthesis and characterization of novel benzothiazole amide derivatives and screening as possible antimitotic and antimicrobial agents

Novel Guanidine Compound against Multidrug-Resistant Cystic Fibrosis-Associated Bacterial Species

Synthesis and Anticancer Evaluation of Some Novel Thiophene, Thieno[3,2‐d]pyrimidine, Thieno[3,2‐b]pyridine, and Thieno[3,2‐e][1,4]oxazepine Derivatives Containing Benzothiazole Moiety

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