Synthesis and biological activity of some new benzoxazoles

Temiz-Arpacı, Özlem; Yıldız, İlkay; Özkan, Semiha Aydın; Kaynak, Fatma; Aki-Sener, Esin; Yalçın, İsmail

doi:10.1016/j.ejmech.2007.09.023

Cited by 46 publications

(22 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The synthesis started with Still cross-coupling reactions and benzothiazole as necessary functionalities for adequate antibacterial activity [44][45][46][47]. For that reason, we decided to use these pharmacophores in the design and synthesis of here reported antibacterial compounds.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and structure–activity relationship of amidine derivatives of 3,4-ethylenedioxythiophene as novel antibacterial agents

Stolić¹,

Paljetak²,

Perić³

et al. 2015

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

Section: Chemistrymentioning

confidence: 99%

Synthesis and structure–activity relationship of amidine derivatives of 3,4-ethylenedioxythiophene as novel antibacterial agents

Stolić¹,

Paljetak²,

Perić³

et al. 2015

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

“…The title compound was obtained by following the same procedure as described for (6) but using (5a) as a starting material instead of (5 …”

Section: -(4-hydroxy-3-nitrophenyl)ethanone (2)mentioning

confidence: 99%

“…Modifications on the benzoxazole nucleus have resulted in a large number of compounds having diverse pharmacological activities [5]. Over the years, several benzoxazole derivatives have been synthesized and screened for their biological activity and many of them have been found to possess good antitubercular activity (Figure 1 [6]- [9].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Biological Evaluation of Novel Antitubercular Agents by Combining Pyrazoline and Benzoxazole Pharmacophores

Soni¹,

Patel²,

Chhabria³

et al. 2016

IJOC

View full text Add to dashboard Cite

Various recent reports on Tuberculosis have alarmed an increase in the patient class and subsequent death rates across the globe. Over and above the spread of more dangerous and fatal forms of tuberculosis like MDR-TB i.e. multiple-drug resistance tuberculosis, XDR-TB i.e. extensively-drug resistance tuberculosis & TDR-TB i.e. total-drug resistance tuberculosis has forwarded an urgent need to discover novel antitubercular agents. The current work is aimed at combining two previously wellknown pharmacophores (pyrazoline and benzoxazole nucleus) in order to design and synthesize a series of novel benzoxazole-based pyrazoline derivatives. The synthesized target compounds were structurally confirmed by LCMS, 1 H-NMR and 13 C-NMR analysis. The target compounds were In vitro evaluated against M. tuberculosis H 37 Rv strain, multidrug-resistant TB (MDR-TB) and extensively drug-resistant TB (XDR-TB) strains. The In vitro screening results depicted that majority of the target compounds displayed potent activity with MIC in a range of ~0.8 to 6.25 μg/mL. Many compounds were found to be more potent than isoniazid against MDR-TB with MIC value 3.12 μg/mL and XDR-TB with MIC value 12.5 μg/mL. Cytotoxicity assay of these active compounds on VERO cell lines also displayed good selectivity index.

show abstract

“…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

View full text Add to dashboard Cite

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.

show abstract

Synthesis and biological activity of some new benzoxazoles

Cited by 46 publications

References 17 publications

Synthesis and structure–activity relationship of amidine derivatives of 3,4-ethylenedioxythiophene as novel antibacterial agents

Synthesis and structure–activity relationship of amidine derivatives of 3,4-ethylenedioxythiophene as novel antibacterial agents

Design, Synthesis and Biological Evaluation of Novel Antitubercular Agents by Combining Pyrazoline and Benzoxazole Pharmacophores

Mechanistic Study on the Formation of Compounds from Thioureas

Contact Info

Product

Resources

About