Synthesis and antifungal activity of 5-arylamino-4,7-dioxobenzo[b]thiophenes

Ryu, Chong Kul; Lee, Su-Kyung; Han, Ju; Jung, Ok-Jai; Lee, Jung Yoon; Jeong, Seong Hee

doi:10.1016/j.bmcl.2005.03.042

Cited by 37 publications

(11 citation statements)

References 8 publications

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“…In accordance with Ram et al [27], strains of Aspergillus fumigatus, Cryptococcus neoformans, Candida albicans, Trichophyton mentagrophytes, and Sporothrix schenckii were sensitive to the analogous thiophene evaluated in the present work. Experiments carried out by Ryu et al [28] demonstrated that synthetic thiophenes possess good activity against A. niger, C. albicans, C. krusei, and C. tropicalis, differing in part of our findings that showed moderate-to-weak antifungal effects against Candida strains. However, Lima et al [29] found growth reduction of dermatophytes, including Trichophyton rubrum, corroborating our results.…”

Section: Discussioncontrasting

confidence: 85%

Incorporation of 2-amino-thiophene derivative in nanoparticles: enhancement of antifungal activity

Neves

Macêdo

et al. 2020

Braz J Microbiol

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The objective of this study was to evaluate the effects of nanoparticles (nanospheres and nanocapsules) of the promising antifungal 2-amino-thiophene (6CN10) and 6CN10 complexed with 2-hydroxypropyl-β-cyclodextrin (6CN10:HP-β-CD) in vitro and compared with free drug against Candida and Cryptococcus, using a microdilution method to measure susceptibility. The Candida and Cryptococcus clinical strains were identified using phenotypic methods and matrix-assisted laser desorption/ ionization-time of flight (MALDI-TOF). To measure in vitro antifungal susceptibility, we used microdilution trials. Serial drug or nanoparticle dilutions were prepared according to the CLSI M27-A3 guidelines. Anti-biofilm activity was verified for Cryptococcus neoformans. All Candida isolates were sensitive to the free drug (MIC = 41.66-333.33 μg/mL) and were able to grow even at the higher concentration tested for all 6CN10 nanoparticles. However, the Cryptococcus neoformans strains presented MIC values of 0.32-83.33 μg/mL for 6CN10 nanoparticles, and MIC values of 0.1-0.2 μg/mL for 6CN10:HP-β-CD nanoparticles, i.e., 3333 times more active than the free drug (MIC values 166.66-333.33 μg/mL), and presenting activity greater than that of the reference drug amphotericin B (MIC = 0.5-0.125 μg/mL). 6CN10:HP-β-CD nanosphere also showed high antibiofilm potential. The in vitro study showed that the nanoparticles allowed better drug efficiency against Cryptococcus than did the free drug. These results suggest that 6CN10-loaded nanoparticles may become a future alternative for cryptococcosis and candidiasis therapy. In vivo experiments are essential prior to clinical use.

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Section: Discussioncontrasting

confidence: 85%

Incorporation of 2-amino-thiophene derivative in nanoparticles: enhancement of antifungal activity

Neves

Macêdo

et al. 2020

Braz J Microbiol

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“…It is also noticed that the antibacterial activities enhance by the present of 2-thienyl ring at position-4 and this might be based on the fact that 2-thiophene has shown an array of biological activities ranging from antibacterial [20][21][22][23][24], antifungal [25,26], antioxidant [27], and anti-inflammatory activity [28].…”

Section: Antibacterial Screeningmentioning

confidence: 99%

Synthesis and Antimicrobial Studies of New Trifluoromethylpyrimidine Analogues

AlNeyadi¹,

Salem²,

Abdou³

2015

JPP

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This paper describes the synthesis of a new series of trifluoromethylpyrimidine and their potential antimicrobial evaluation. We have prepared 10 novel pyrimidine derivatives in high yields and short reaction time using microwave irradiation. Compounds 4a,b and 6a,b showed good antimicrobial activity against Gram-positive bacteria; Clostridium perfringens, Bacillus pumilus and Enterococcus faecalis. These compounds were found to be the most potent antimicrobials compared to ampicillin, tetracycline, and streptomycin that showed no activity against Enterococcus faecalis. Compounds 4a,b and 6a,b exhibited great antimicrobial potency against all tested bacteria strains at a MIC of 3.125-100 μg/mL whereas only 4a showed the antimicrobial activity against Gram-negative bacteria Klebsiella pneumonia with a MIC value 12.5 μg/mL.

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“…Nowadays benzothiophene derivatives in combination with other ring systems have been used extensively in pharmaceutical applications. [1][2][3] A large number of compounds containing thiophene system have been investigated because of their broad spectrum of biological activities which include analgesic, 4 antibacterial, 5 antifungal, 6 antiparasitic, 7 antiviral, 8 anti-inflammatory, 9 anticonvulsant, 10 anti-nociceptive, 11 DNA cleavage, 12 herbicidal, 13 antitubercular, 14 protein kinase inhibition, 15 respiratory syndrome protease inactivation, 16 an active ester in the peptide synthesis and agonists of peroxisome proliferator activated receptors. 17 In addition to these considerable biological applications, tetrahydrobenzo [b]thiophenes are important intermediates, protecting groups and final products in organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, cytotoxic and anti-proliferative activity of novel thiophene, thieno[2,3-b]pyridine and pyran derivatives derived from 4,5,6,7-tetrahydrobenzo[b]thiophene derivative

Mohareb

Abdo

Al-farouk

2017

ACSi

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Novel tetrahydrobenzo [b]thienopyrole derivatives are synthesized from 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene (1) through its reaction with α-chloroacetone to give the corresponding N-alkyl derivative 3. Compound 3 undergoes ready cyclization in sodium ethoxide solution to give the tetrahydrobenzo[b]thienopyrrole 4. The latter compound 4 is used as the key starting material for the synthesis of thiophene, thieno [2,3-b]pyridine and pyran derivatives. The cytotoxicity of the synthesized products towards the human cancer cell lines namely gastric cancer (NUGC), colon cancer (DLD-1), liver cancer (HA22T and HEPG-2), breast cancer (MCF-7), nasopharyngeal carcinoma (HONE-1) and normal fibroblast (WI-38) cell lines are measured. Compounds 4, 7a, 7b, 8a, 8b, 10c, 10d, 10f, 12a, 12b, 14b and 15b exhibit the optimal cytotoxic effect against cancer cell lines. Compounds 7b and 14b show the maximum inhibitory effect and these are much higher than the reference CHS-828 (pyridyl cyanoguanidine). On the other hand, the anti-proliferative evaluations of these compounds with high potency against the cancer cell lines L1210, Molt4/C8, CEM, K562, K562/4 and HCT116 show that compounds 7b and 8b give IC 50 's against Molt4/C8 and CEM cell lines higher than that of the reference, doxorubicin.

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Synthesis and antifungal activity of 5-arylamino-4,7-dioxobenzo[b]thiophenes

Cited by 37 publications

References 8 publications

Incorporation of 2-amino-thiophene derivative in nanoparticles: enhancement of antifungal activity

Incorporation of 2-amino-thiophene derivative in nanoparticles: enhancement of antifungal activity

Synthesis and Antimicrobial Studies of New Trifluoromethylpyrimidine Analogues

Synthesis, cytotoxic and anti-proliferative activity of novel thiophene, thieno[2,3-b]pyridine and pyran derivatives derived from 4,5,6,7-tetrahydrobenzo[b]thiophene derivative

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