Synthesis of some novel 2-substituted benzoxazoles as anticancer, antifungal, and antimicrobial agents

Jauhari, P. K.; Bhavani, A. K. D.; Varalwar, Subhash; Kiran, Shumaila; Raj, Prem

doi:10.1007/s00044-007-9076-x

Cited by 36 publications

(26 citation statements)

References 25 publications

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“…Potent benzoxazoles showing HIV reverse transcriptase inhibition were reported by Medebielle and colleagues and these products presented antifungal activities against Aspergillus niger and A. flavus [6]. In 2008, Jauhari and colleagues described the cytotoxic activity of 2 Journal of Chemistry synthetic benzoxazoles against cervical, colon, and breast adenocarcinoma cell lines [7], while Arisoy and contributors described the relevant activities of 2,5-disubstituted benzoxazoles against Candida krusei and gentamicin-resistant isolates of Pseudomonas aeruginosa [8]. Kim et al (2010) have prepared benzoxazole amides, which presented good activity against Malassezia furfur, a pathogenic fungus, involved in fatal sepsis cases [9].…”

Section: Introductionmentioning

confidence: 97%

Antifungal Activity of New Eugenol-Benzoxazole Hybrids against Candida spp.

Carvalho

Alvarenga

Carmo

et al. 2017

Journal of Chemistry

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Eugenol is a natural allylphenol responsible for a wide range of biological activities, especially antimicrobial. Benzoxazoles are heterocycles with recognized antimicrobial activities. This paper describes the design, synthesis, and the biological results for benzoxazole type derivatives of eugenol as antifungal agents. The products were obtained in good yields by a four-step synthetic sequence involving aromatic nitration, nitroreduction, amide formation, and cycle condensation. They were evaluated against species of Candida spp. in microdilution assays, and four products (5a, 5b , 5c, and 5d ) were about five times more active than eugenol against C. albicans and C. glabrata. Two of them (5b and 5d ) showed good activity against C. krusei, a species which is naturally resistant to fluconazole. Furthermore, the active products were more selective than eugenol against human blood cells, showing that they are interesting substances for further optimization.

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Section: Introductionmentioning

confidence: 97%

Antifungal Activity of New Eugenol-Benzoxazole Hybrids against Candida spp.

Carvalho

Alvarenga

Carmo

et al. 2017

Journal of Chemistry

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“…Benzoxazoles are a class of heterocyclic compounds exhibiting therapeutical activities (Figure 2), such as, antifungal agents [38][39][40], cytotoxic compounds [41], as anti-inflammatory agents [42], as HIV-1 protease inhibitor [43], as an antibiotic [44], as CpIMPDH inhibitors [45], nonnucleoside HIV-1 reverse transcriptase inhibitors (NNRTI) [46], and antitumour agents [47].…”

Section: Benzoxazole Amides From Benzoylthioureasmentioning

confidence: 99%

Mechanistic Study on the Formation of Compounds from Thioureas

Laitonjam¹,

Nahakpam²

2018

Density Functional Calculations - Recent Progresses of Theory and Application

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Formation of 2-(N-arylamino)benzothiazole takes place, when N,N 0 -diphenylthioureas are treated with polymer-supported tribromide or with iodine-alumina as catalyst under solvent free conditions. However, when N-substituted-N 0 -benzoylthioureas are treated with polymer-supported tribromide or with iodine-alumina as catalyst either under various conditions or under solvent free conditions, decomposition takes place to give the respective benzamides and thiobenzamides. Mechanistic study of the formation of these compounds is studied using DFT calculations. It is found that electron donating group at the para-position of the aryl group of benzoylthiourea favors the formation of benzamide whereas the presence of electron withdrawing group at para-position of the aryl group of benzoylthiourea, formation of thiobenzamide takes place. When the catalyst is changed to diacetoxyiodobenzene (DIB) under similar reaction conditions, benzoxazole amides are formed; expected benzothiazoles or the decomposition products are not obtained. Mechanistic study of the reaction using DFT calculation again shows that the reaction followed through carbodiimide intermediate undergoes the formation of C-O bond in benzoxazole moiety, instead of the expected C-S bond formation of benzothiazole moiety via a sequential acylation and deacylation process.

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“…The synthesized compounds 5a-k, 8, and 9a-f were subjected to cytotoxicity study using cancer cells of various origins as several reports indicate that benzoxazole derivatives show potent anti-cancer activity (Kumar et al, 2002;Easmon et al, 2001;Jauhari et al, 2008;Rida et al, 2005). The cytotoxicity studies of the compounds were determined against four human cancer cell lines using MTT assay as described earlier (Smitha et al, 2005), and the results were presented in the Fig.…”

Section: Antiproliferative Activitymentioning

confidence: 99%

“…Benzoxazole derivatives are biologically significant compounds and are known to exhibit various biological activities, such as anticancer (Kumar et al, 2002;Easmon et al, 2001;Jauhari et al, 2008;Rida et al, 2005), antimicrobial (Kumar et al, 2002;Temiz-Arpacı et al, 2005), anti HIV (Rida et al, 2005;Temiz-Arpacı et al, 2005) and dopamine D4 agonists (Wang et al, 2005). The substitution at second position in benzoxazole skeleton is influential for the biological activity of the molecule.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and preliminary evaluation of 2-substituted-1,3-benzoxazole and 3-[(3-substituted)propyl]-1,3-benzoxazol-2(3H)-one derivatives as potent anticancer agents

et al. 2010

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The synthesis and cytotoxic activity studies of a new series of cyclic amine containing benzoxazole and benzoxazolone derivatives are described. The 2-cyclic amine-1,3-benzoxazoles 5a-k, 5-chloro-3-(3-chloropropyl)-1,3-benzoxazol-2(3H)-one 8 and 3-[3-(cyclic amino)-propyl]-1,3-benzoxazol-2(3H)-ones 9a-f were synthesized. The newly synthesized compounds with the influence of the presence of cyclic amine moiety in the benzoxazole scaffold have been evaluated with respect to their cytotoxic effect toward four human cancer cell lines. The new compounds were evaluated to see whether substitution at the second and third position of the benzoxazole motif influence their cytotoxic effect toward cancer cells.

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Synthesis of some novel 2-substituted benzoxazoles as anticancer, antifungal, and antimicrobial agents

Abstract: Benzoxazole derivatives show various types

Cited by 36 publications

References 25 publications

Antifungal Activity of New Eugenol-Benzoxazole Hybrids against Candida spp.

Antifungal Activity of New Eugenol-Benzoxazole Hybrids against Candida spp.

Mechanistic Study on the Formation of Compounds from Thioureas

Synthesis and preliminary evaluation of 2-substituted-1,3-benzoxazole and 3-[(3-substituted)propyl]-1,3-benzoxazol-2(3H)-one derivatives as potent anticancer agents

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