Synthesis and investigation of antibacterial activities and carbonic anhydrase and acetyl cholinesterase inhibition profiles of novel 4,5-dihydropyrazol and pyrazolyl-thiazole derivatives containing methanoisoindol-1,3-dion unit

BUDAK, YAKUP; Kocyigit, Umit M.; GÜRDERE, MELİHA BURCU; Ozcan, Kezban; Taslimi, Parham; Gulcin, Ilhami; CEYLAN, MUSTAFA

doi:10.1080/00397911.2017.1373406

Synthesis and investigation of antibacterial activities and carbonic anhydrase and acetyl cholinesterase inhibition profiles of novel 4,5-dihydropyrazol and pyrazolyl-thiazole derivatives containing methanoisoindol-1,3-dion unit

Yazarlar (7)

Prof. Dr. Yakup BUDAK Tokat Gaziosmanpaşa Üniversitesi, Türkiye

Umit M. Kocyigit
Cumhuriyet Üniversitesi, Türkiye

Prof. Dr. Meliha Burcu GÜRDERE Tokat Gaziosmanpaşa Üniversitesi, Türkiye

Kezban Ozcan
Tokat Gaziosmanpaşa Üniversitesi, Türkiye

Parham Taslimi
Atatürk Üniversitesi, Türkiye

Ilhami Gulcin
Atatürk Üniversitesi, Türkiye

Prof. Dr. Mustafa CEYLAN Tokat Gaziosmanpaşa Üniversitesi, Türkiye

Makale Türü	Özgün Makale
Makale Alt Türü	SSCI, AHCI, SCI, SCI-Exp dergilerinde yayınlanan tam makale
Dergi Adı	Synthetic Communications
Dergi ISSN	0039-7911 Wos Dergi Scopus Dergi
Dergi Tarandığı Indeksler	SCI-Expanded
Dergi Grubu	Q4
Makale Dili	İngilizce
Basım Tarihi	11-2017
Cilt No	47
Sayı	24
Sayfalar	2313 / 2323
DOI Numarası	10.1080/00397911.2017.1373406
Makale Linki	https://www.tandfonline.com/doi/full/10.1080/00397911.2017.1373406

Özet

Novel 4,5-dihydropyrazole derivatives (3a–i), 3-(4-((3aR,4S,7R,7aS)-1,3-dioxo-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindol-2(3H)-yl)phenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-1-carbothio amide, were obtained by the addition of thiosemicarbazide (2) to the chalcones (1a–i). The addition–cyclization of 2,4′-dibromoacetophenone (4) to pyrazole derivatives (3a–i) gave the new pyrazolyl-thiazole derivatives (5a–i), (3aR,4S,7R,7aS)-2-(4-(1-(4-(4-bromophenyl)thiazol-2-yl)-5-phenyl-4,5-dihydro-1H-pyrazol-3-yl)phenyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione. Antibacterial and acetylcholinesterase (AChE) enzyme and human carbonic anhydrase (hCA) I, and II isoform inhibitory activities of the compounds 3a–i and 5a–i were investigated. Some of the compounds showed promising antibacterial activity. In addition, the hCA II and I were effectively inhibited by the lately synthesized derivatives, with Ki values in the range of 18.90 ± 2.37 −58.25 ± 13.62 nM for hCA II and 5.72 ± 0.98 −37.67 ± 5.54 nM for hCA I. Also, the Ki parameters of these compounds for AChE were obtained in the range of 25.47 ± 11.11 − 255.74 ± 82.20 nM. Also, acetazolamide, clinical molecule, was used as a CA standard inhibitor that showed Ki value of 70.55 ± 12.30 nM against hCA II, and 67.17 ± 9.1 nM against hCA I, and tacrine inhibited AChE showed Ki value of 263.67 ± 91.95.

Anahtar Kelimeler

Acetylcholinesterase | antibacterial activity | carbonic anhydrase | pyrazole | pyrazolyl-thiazole

BM Sürdürülebilir Kalkınma Amaçları

Atıf Sayıları
WoS	40
SCOPUS	40

Synthesis and investigation of antibacterial activities and carbonic anhydrase and acetyl cholinesterase inhibition profiles of novel 4,5-dihydropyrazol and pyrazolyl-thiazole derivatives containing methanoisoindol-1,3-dion unit

Dergi Adı	SYNTHETIC COMMUNICATIONS
Yayıncı	Taylor and Francis Ltd.
Açık Erişim	Hayır
ISSN	0039-7911
E-ISSN	1532-2432
CiteScore	4,3
SJR	0,322
SNIP	0,560

Synthesis and investigation of antibacterial activities and carbonic anhydrase and acetyl cholinesterase inhibition profiles of novel 4,5-dihydropyrazol and pyrazolyl-thiazole derivatives containing methanoisoindol-1,3-dion unit

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