Novel 1,4-naphthoquinone N-aroylthioureas: Syntheses, crystal structure, anion recognition properties, DFT studies and determination of acid dissociation constants
Gemili, Müge | Nural, Yahya
In this paper, five novel 1,4-naphthoquinone N-aroylthiourea derivatives were synthesized, by the reaction of 2,3-diaminonaphthalene-1,4-dione and aroylisothiocyanates, in excellent yield (88-96%) and characterized by using FT-IR, H-1/C-13 NMR and HRMS. In addition, the molecular structure of one of the 1,4-naphthoquinone N-aroylthiourea compounds was characterized by single crystal X-ray diffraction studies. The absorption spectra of the compounds were determined in DMSO and the dyes have absorption in visible region in the range of 464-477 nm. The chemosensing ability of each of the prepared dyes was assessed by titrating them towards the anions; F-, Cl-, Br-, I- AcO-, CN-, CIO4-, H2PO4-, HSO4-, and NO3-, using spectrophotometric and H-1 NMR titration techniques in DMSO, experimentally. ...
Potansiyel biyoaktif polisübstitüe yeni aminokarbotiyol pirolidin bileşiklerinin sentezi, kristal yapısı ve antimikrobiyal özelliklerinin incelenmesi
İnce, Tuncay | Nural, Yahya | Döğen, Aylin | Serin, Mehmet Sami | Döndaş, Hacı Ali
Potansiyel biyoaktif polisübstitüe yeni aminokarbotiyol pirolidin bileşiklerinin sentezi, kristal yapısı ve antimikrobiyal özelliklerinin incelenmesi
New naphthoquinone thiazole hybrids as carbonic anhydrase and cholinesterase inhibitors: Synthesis, crystal structure, molecular docking, and acid dissociation constant
Efeoğlu, Çağla | Selçuk, Özge | Demir, Bünyamin | Nural, Yahya
In this study, N-[3-(3-amino-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-R-thiazol-2(3H)-ylidene]-2,6-difluorobenzamide derivatives as new 1,4-naphthoquinone thiazole hybrids were synthesized by reacting of N-[(3-amino-1,4-dioxo-1,4-dihydronaphthalen-2-yl)carbamothioyl]-2,6-difluorobenzamide with various α-bromoketones in 76–92% yields. Their molecular structures were characterized by 1H NMR, 13C NMR, 19F NMR, FT-IR, and HRMS, and the stereochemistry of one of the hybrids was determined by single crystal x-ray diffraction study. These synthesized new compounds (3a–e) were found to be effective inhibitor molecules for cholinesterases (butyrylcholinesterase (BChE) and acetylcholinesterase (AChE)), and carbonic anhydrase I and II (hCA I and hCA II) enzymes. KI values were found to be in the range...
Pirolidin halkası bulunduran fused yapıda tiyohidantoin türevi bileşiklerin sentezi ve Karakterizasyonu
Nural, Yahya | Döndaş, Hacı Ali
Tiyohidantoin türevleri, biyoaktif özelliklere sahip olmalarndan dolay , ilaç ve zirai kimyada yayg n olarak kullan lan önemli bir bile ik snfn olutururlar [1]. Tiyohidantoin analoglar antimikrobiyal [1,2], antitümöral [3], antiviral [4] ve antikonvulsant [5] gibi çe itli farkl etkilere sahip olduklar literatürde bilinmektedir. Termal veya metal katalizörlü imin-azometin yilür 1,3-dipolar halkal katlma reaksiyonlar sonucu elde edilen MK-329 analou olan spirobenzodiazepenler [6], nikkomisin analoglar [7], peptidomimetikler [8] gibi potansiyel biyoaktif özelliklere sahip pirolidin türevi bile ikler literatürde yer almaktadr. Pirolidin halkas, antimikrobiyal özellik gösteren baz bile iklerin yaplarnda da bulunmaktadr [9]. Bu çal mada, biyoaktivite için önemli olabilecek ve d...
New naphthoquinone thiazole hybrids as carbonic anhydrase and cholinesterase inhibitors: Synthesis, crystal structure, molecular docking, and acid dissociation constant
Efeoğlu, Çağla | Selçuk, Özge | Demir, Bünyamin | Nural, Yahya
In this study, N-[3-(3-amino-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-R-thiazol-2(3H)-ylidene]-2,6-difluorobenzamide derivatives as new 1,4-naphthoquinone thiazole hybrids were synthesized by reacting of N-[(3-amino-1,4-dioxo-1,4-dihydronaphthalen-2-yl)carbamothioyl]-2,6-difluorobenzamide with various α-bromoketones in 76–92% yields. Their molecular structures were characterized by 1H NMR, 13C NMR, 19F NMR, FT-IR, and HRMS, and the stereochemistry of one of the hybrids was determined by single crystal x-ray diffraction study. These synthesized new compounds (3a–e) were found to be effective inhibitor molecules for cholinesterases (butyrylcholinesterase (BChE) and acetylcholinesterase (AChE)), and carbonic anhydrase I and II (hCA I and hCA II) enzymes. KI values were found to be in the range...
Polysubstituted pyrrolidines linked to 1,2,3-triazoles: Synthesis, crystal structure, DFT studies, acid dissociation constant, drug-likeness, and anti-proliferative activity
İnce, Tuncay | Demir, Bünyamin | Erat, Selma | Nural, Yahya
Novel pyrrolidines linked to 1,2,3-triazole derivatives, dimethyl 1-(2-(4-R-1H-1,2,3-triazol-1-yl)acetyl)-5,5-diphenylpyrrolidine-2,4-dicarboxylate, were synthesized in the presence of sodium ascorbate and copper (II) sulfate pentahydrate by click chemistry in excellent 89–95% yield. The 1H NMR, 13C NMR, DEPT, COSY, HMQC, FT-IR, HRMS and elemental analysis techniques were used for structural characterization. A single crystal X-ray diffraction study was performed in order to determine the stereochemistry of the compounds. The optimization geometry of the compounds was obtained by performing density functional theory. However, the global reactivity parameters were estimated from frontier molecular orbitals. The calculated global reactivity parameters showed that the most reactive compound w...
1,4-Naphthoquinone thiazoles: Synthesis, crystal structure, anti-proliferative activity, and inverse molecular docking study
Efeoğlu, Çağla | Demir, Bünyamin | Yabalak, Erdal | Nural, Yahya
In this study, 1,4-naphthoquinone thiazole hybrids were synthesized by reacting 1,4-naphthoquinone thioureas with various α-bromoketones in 78–86 % yields and characterized using 1H NMR, 13C NMR, FT-IR, and HRMS techniques. Furthermore, single crystal x-ray diffraction studies were also performed for 3b and 3c hybrids to determine stereochemistry. Density Functional Theory (DFT) calculations were performed to obtain additional information and to support the x-ray studies. The in vitro anti-proliferative activities of 1,4-naphthoquinone thiazoles were investigated against PC3 human prostate cancer cells. The products 3a–h showed anti-proliferative activity against PC3 cells, and the cell viability studies showed that the IC50 values of compounds 3f and 3e were 20.10 µM and 21.14 µM, respect...