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. ...

Synthesis of novel aminocarbo-N-thiol pyrrolidine derivatives and their antituberculosis activities

Poyraz, Samet | Nural, Yahya | Ülger, Mahmut | Belveren, Samet | Gemili, Müge | Erşen, Duygu | Serin, Mehmet Sami | Döndaş, Hacı Ali

Pyrrolidine and aminocarbothiol pyrrolidine derivatives have been extensively studied during the last decade due to possessing biological and pharmacological properties such as antifungal, antibacterial and antimalarial activity [1-3]. Pyrrolidine ring also have important place in drug research and this structure is present in many alkaloids and drug molecules [1].

Synthesis of Highly Functionalized 2-(Thiazol-2-yl)-octahydropyrrolo[3,4-c]pyrrole Derivatives Using Subcritical Water

Gemili, Müge | Nural, Yahya | Yabalak, Erdal

Thiazole and pyrrolidine derivatives are among the most important pharmacophore groups in drug research studies.1,2 It is known that both thiazole3 and pyrrolidine4 moieties are present in a wide range of pharmacologically active compounds. Subcritical water is a green alternative to conventional solvents because of being an environmentally friendly, cheap, safe and non-toxic solvent.5 Subcritical water offers the unique medium for performing various organic reactions.6 In this study, we designed and synthesized a series of novel 2-(thiazol-2-yl)-octahydropyrrolo[3,4-c]pyrrole derivatives in subcritical water in highly to excellent yield.

Synthesis of Polysubstituted Methyl 5,5-diphenyl-1-(thiazol-2-Yl)pyrrolidine-2-carboxylate Derivatives Using scCO2

Nural, Yahya | Gemili, Müge | Yabalak, Erdal

Thiazole core has been intensively studied in the drug research field, due to the fact that the compounds containing this moiety exhibited various pharmacological activity.1 The other important pharmacophore group, pyrrolidine core, has been also intensively studied in pharmaceutical chemistry.2 The environmentally friendly supercritical carbon dioxide (scCO2) is one of the most widely used fluids3, and has been extensively used as an organic solvent4 due to having significant advantages such as low toxicity, non-flammability and changeable physical properties, as well as can be easy separated from reaction medium.3,4 It is known that scCO2 has been used in various reactions such as in chemo-, regio-, and enantioselective,5 and many other organic synthetic reactions.6 In this...

1,4-Naftokinon yapısı bulunduran yeni bileşiklerin sentezi, asit dissosiyasyon sabitlerinin belirlenmesi, kemosensör özelliklerinin ve antimikrobiyal aktivitelerinin incelenmesi

Gemili, Müge

Bisiklik aminokarbo-n-tiyol pirolidin türevi bileşiklerin bazı metal kompleksleri ve oluşum sabitlerinin incelenmesi

Gemili, Müge

Green synthesis of highly functionalized octahydropyrrolo[3,4-c]pyrrole derivatives using subcritical water, and their anti(myco)bacterial and antifungal activity

Nural, Yahya | Gemili, Müge | Yabalak, Erdal | Ulger, Mahmut

A series of novel 2-(thiazol-2-yl)-octahydropyrrolo[3,4-c]pyrroles was synthesized by reaction of octahydropyrrolo[3,4-c]pyrrole N-benzoylthiourea derivatives and alpha-haloketones in subcritical water at 130 degrees C in 75-91% yield. Both the thiourea intermediates and the end productswere synthesized in subcritical water, which proved a suitable green alternative to acetone by delivering the desired compounds in much shorter reaction times and practically the same yields. The antimicrobial activity of the compounds was determined against five bacterial strains and three fungal strains, and MIC values of 15.62-250 mu g/mL were observed. Moreover, the compounds exhibited antimycobacterial activity against M. tuberculosis H37Rv with MIC values of 7.81-62.5 mu g/mL.

Tetrahidropirolo[3,4-b]pirol-4,6(5H,6aH)-dion Türevi Bileşiklerin Sentezi ve Karakterizasyonu

Nural, Yahya | Belveren, Samet | Gemili, Müge | Döndaş, Hacı Ali

Pirolidin halkasl bulunduran bazl bi|eşikler, antitümör, antimikrobiyal ve antidepresan etkilerinin yanı slra baıllannln glıkosıdaz Ve HcV Ns3/4A proteaz enzim anhibitÖr Özellİği 865terdikleri rapo, €dilmiştil 11] Pirolidin türevi bileşiklerin 1,3-dipolar halkall katlıma tepkimeleri ile re8io ve streospesifik olalak senteıie; sonucu potansiyel biyoaktif çeşitli nikkomisin anaIo8lan, peptidomimetik|er ve pirolidin halka$ bulunduhn basiklik tiyohidantoin türevi bileşaklerin de elde edildikleri literatürde yer almaktadlr [2]. Bu çallşmada, l,3_dıpolar halkall katılma tepkimesi sonucu elde edilen İused Yaplda bisiklik pirolidin tİrevi tetrahidropiroloı3,4-c]piro|-1,3 (2H,3aH}-djon bileşiklerinden, halka düıenlenmesi sonucu tetrahıdropirolol3,4_b]piro1-4,6 (5H,6a8)-dion türevi yeni pir...

Polisübstitüe metil 2-(benzoilkarbamotiyol)-4,6-diksooktahidropirolo[3,4-c]pirol-1-karboksilat türevlerinin asit iyonlaşma sabitlerinin belirlenmes

Gemili, Müge | Nural, Yahya | Döndaş, Hacı Ali

Asit iyonlaşrna sabiti (pK.), molekiili.in asitliği, çtizünebilirliği, lipofilikliğ ile birlikte birçok özelliğ hakhnda bilgiler veren önemli bir parametredirl. Ayrıca, biı ilacın eıki edeceği bölgeye taşınması, bölgedeki derişiıni gibi bilgilerin yaıı sır4 ilaçlaruı iyonik ve iyon{ipol bağlan yaparak reseptörle etkileştiğ dikkate alınüğında asitlik sabilinin önemi düa da artmaktadır'. Biyoaktif özellik gösteren bileşiklerin çok büyük bir krsmı yapılannda azot atomu bulundurmakta ve ilaç Aı{e çalışmalannda azot atomu bulunduıan bileşikler önemli bir yer teşkil etmektedir. Yapısında bir azot atomu bu[unduran beş üyeli heterosiklik bir yapıda olan pirolidin halkası ve tiirevleri ilaç araştırmalannuı en önerıli aıaştırma alanlanndan biridir]. Bu çalışmada daba önceki çatışmalanmı...

Fused yapıda pirolidin-pirolidindion halka sistemi sübstitüentli N-karbamotiyolbenzamid türevlerinin Pt(II) ve Ni(II) komplekslerinin oluşum sabitlerinin belirlenmesi

Gemili, Müge | Nural, Yahya | Döndaş, Hacı Ali

Kompleks kararlılık sabiti olarak bilinen kompleks oluşum sabitteri, ınetallerin ve ligandlann kompleks oluşturma istekleri, koordinasyonlan, kompleks molekiillerin çöziiniirliikleri gibi birçok özellikleri hakkında bilgi vermehcdirı. Metal-ligand kararlılık sabitleri potansiyomelrik, spektrofotomctrik ve kondiiltometrik gibi farktı birçok yöntemle bclirlenebitmektedir'. Geçiş mctali komplckslerinin biyolojik §isteırıleldcki farmakolojik özelliklerinden dolay farmasötik kimyada önemli bir role sahiptir3. Bıınırnta biılikte, geniş spektrum biyotojik özelliktere sahip olduğu bilinen y'y'-Karbamotiyolbenza mid tiirevlerinin sensör ve saflaşürma için uygunluklanndan dolayı analitik kimyada ve komplekslcşmeye yatkınlıklanndan dolay kooıdinasyon kimyasında da gün geçtikçe ...

Environmentally friendly synthesis of N-thiazole-pyrrolidine derivatives in supercritical carbon dioxide and subcritical water

Nural, Yahya | Yabalak, Erdal | Belveren, Samet | Gemili, Müge | Gizir, Ahmet Murat | Döndaş, Hacı Ali

The environmentally friendly supercritical carbon dioxide (scCO2) is one of the most widely used fluids and its low toxicity, non-flammability and easy seperation from reaction medium make it favoured for the synthetic green chemistry [1a,b]. It has been reported that scCO2 is a good solvent for various chemical reactions such as in enzymatic catalysis reactions and organometallic catalysis reactions [1]. Cobalt is essential metal in all living organisms [2] and some Co(III) complexes have shown broad spectrum bioactivity [3]. Benzoylthiourea derivatives are known as important class of both heterocyclic and coordination chemistry [4]. In previous study [5], we have reported the synthesis of polysubstituted aroylaminocarbo-N thiol pyrrolidines derivatives and their Ni(II), Pd...

Bisiklik aminokarbo-N-tiyol pirolidin türevi bileşiklerin bazı metal kompleksleri ve oluşum sabitlerinin incelenmesi

Gemili, Müge

Bu çalışmada pirolidin ve N-sübstitüe pirolidin-2,5-dion halkalarını fused yapıda bulunduran tetrahidropirolo[3,4-c]pirol-1,3(2H,3aH)-dion halka sistemi sübstitüentli arilaminokarbo-N-tiyol türevi yeni ligandların Pt(II) ve Ni(II) kompleksleri sentezlendi. Ligandların asit iyonlaşma sabitleri ve metal komplekslerinin oluşum sabitleri potansiyometrik titrasyon metoduyla belirlendi. Çalışmanın birinci aşamasında, tetrahidropirolo[3,4-c]pirol(2H,3aH)-1,3-dion halka sistemli arilaminokarbo-N-tiyol türevi yeni bileşikler ve bu bileşiklerin Ni(II) ve Pt(II) kompleksleri sentezlenerek yapıları ve stereokimyaları tek kristal XRD, çeşitli NMR teknikleri, FT-IR ve MS ile belirlendi. İkinci aşamada, arilaminokarbo-N-tiyol türevlerinin 2x10-4 M'lık derişimlerinde, asetonitril-su (25:75 v/v) hidro...

Environmentally friendly synthesis of N-thiazole-pyrrolidine derivatives in supercritical carbon dioxide and subcritical water

Nural, Yahya | Yabalak, Erdal | Gemili, Müge | Gizir, Ahmet Murat | Döndaş, Hacı Ali

Supercritical carbon dioxide (scCO2) is widely used in several academic discipline as environmentally friendly fluid. Studies related to scCO2 have gained importance, due to having some properties such as low toxicity and non-flammability [1]. Subcritical water is defined as water which heated between 100 and 374 °C and pressurized high enough to maintain it in the liquid state [2] Solvent properties which related to polarity of water is depend on its temperature. As a result both polar and non-polar organics can easily dissolve in subcritical water [3]. Thiazole [4] and pyrrolidine [5], five-membered heterocyclic structures, have been intensively studied in medicinal chemistry because of their heterocyclic moieties in which present in the many bioactive molecules and alkal...

1,4-naftokinon yapısı bulunduran yeni bileşiklerin sentezi, asit dissosiyasyon sabitlerinin belirlenmesi, kemosensör özelliklerinin ve antimikrobiyal aktivitelerinin incelenmesi

Gemili, Müge

Bu çalışma kapsamında, 1,4-naftokinon yapısı bulunduran yeni bileşikler olarak 1,4-naftokinon N-aroiltiyoüre türevi bileşikler ile 1,4-naftokinon 2-iminotiyazol türevi bileşikler sentezlendi. 1,4-Naftokinon N-aroiltiyoüre türevi bileşikler, 2,3-diaminonaftalen-1,4-dion ve aroilizotiyosiyanatların reaksiyonu ile yüksek verimle (%88-96) sentezlendi ve yapıları, 1H/13C NMR, FT-IR ve HRMS gibi analitik tekniklerle karakterize edildi. Sentezlenen 1,4-naftokinon N-aroiltiyoüre bileşiklerinden 76b'nin moleküler yapısı tek kristal X-ışını kırınım tekniği ile tamamen aydınlatıldı. 1,4-Naftokinon N-aroiltiyoüre türevi bileşiklerin kemosensör özellikleri, F, Cl, Br, I, AcO, CN, ClO4, H2PO4, HSO4 ve NO3 anyonlarına karşı dimetil sülfoksit çözücüsünde UV-görünür bölge spektrofotometrik ve 1H NMR s...

Potentiometric Determination of Acid Dissociation Constants of 2-(pyrrolidin-1-yl)thiazole Derivatives

Nural, Yahya | Gemili, Müge

Physicochemical parameters provide critical information for scientists in the many scientific fields such as drug research studies, the development of analysis methods, etc [1]. The acid dissociation constant (pKa) is one of the most important physicochemical parameters [1-3]. In this study [4], acid dissociation constants of the potential bioactive 2-(pyrrolidin-1-yl)thiazole derivatives were potentiometrically determined at 25.0 ± 0.1 ºC in a 30% (v/v) DMSO-water mixture. The potentiometrically obtained data were used for the calculation of the pKa values using the HYPERQUAD computer program. Three different pKa values were found for the compounds and the pKa1, pKa2 and pKa3 values were obtained in a range of 2.46 (±0.10) - 3.78 (±0.10), 5.61 (±0.07) - 6.77 (±0.08) and 8.50...

Antiapoptotic Effect of Pyrrolidine Derivatives Bearing Indole Ring As Substituted Moiety on MCF-7 Cells

Nural, Yahya | Canacankatan, Necmiye | Belveren, Samet | Poyraz, Samet | Gemili, Müge | Yetkin, Derya | Kibar, Kezban | Yılmaz, Ş. Necat | Döndaş, Hacı Ali

Background: The pyrrolidine and indole ring system found in the structure of various biologically important compounds used in the treatment of various diseases (1) and has a significant place in the pharmaceutical R&D studies (2). Thus the combination of the two ring system into compounds; A and B were attractive, we studied apoptotic effect of these compounds on the human breast cancer MCF-7 cells. The balance between cell proliferation and apoptosis is very important in the formation of cancer. Caspases are the major executioners which lead to apoptotic cell death. Caspases 8 and 9 are the most important members of this group (3). Methods: Pyrrolidine derivatives bearing the indole ring have been synthesized and characterized as indicated our previous studies (4). Three rep...