Synthesis and Some Reactions of Pyrazole-3-carboxylic acid Having Trifluoromethyl Unit
Yıl: 2019 Cilt: 9 Sayı: 4 Sayfa Aralığı: 645 - 654 Metin Dili: İngilizce DOI: 10.17714/gumusfenbil.528165 İndeks Tarihi: 12-02-2021
Synthesis and Some Reactions of Pyrazole-3-carboxylic acid Having Trifluoromethyl Unit
Öz: 4-benzoyl-5-phenyl-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carboxylic acid 2 was obtained from 4-benzoyl-5-phenyl-2,3-furandione 1 and (4-(trifluoromethyl)phenyl) benzaldehyde-phenyl hydrazone 1a. Obtained new pyrazolecarboxylic acid derivative was converted into acid chloride form. Reaction of new derivatives between acid chlorideand some of nucleophiles were progressed. The esters (4a-c) were obtained using Schotten Baumann method with thecorresponding alcohols and acid chloride (3). Pyrazolopiridazinone derivatives (8, 9, 10) were obtained as a result ofcyclization reactions between pyrazole carboxylic acid and various hydrazines. Additionally, reactions between an acidechloride 3 and certain amines and ureas were carried out to yield amides (5a, 5b-f) and carbo-urea (6a-c) derivatives.The nitrile compound (7) was also synthesized from the amine compound via the removal of water with the use ofSOCl2 and DMF. All synthesized molecules were subjected to antibacterial activity to see their potential as unknownreagent. 6-nitro-3,4-diphenyl-2-(4-(trifluoromethyl)phenyl)-2,6-dihydro-7H-pyrazolo[3,4-d]pyridazin-7-one (10)showed antibacterial activity against only the Gram-positive bacteria, Bacillus cereus and Micrococcus luteus, with aMIC value of 32 and 128 µg/mL, respectively. This finding revealed that functional group is important for antibacterialactivity. Compound 10 having a nitro group inhibited growing of bacteria more than positive control, streptomycin intwo different types of bacteria. This might be a good clue for further investigation about antibacterial agents.
Anahtar Kelime: Triflorometil Grubuna Sahip Pirazol-3-karboksilik Asit Sentezi ve Bazı Tepkimeleri
Öz: 4-Benzoil-5-fenil-2,3-furandion 1 ve (4-(triflorometil)fenil) benzaldehit-fenil hidrazonun 1a reaksiyonundan 4-benzoil5-fenil-1-(4-(triflorometil)fenil)-1H-karboksilik asit 2 elde edildi. Elde edilen yeni pirazol karboksilik asit (2) türevi, asit klorürüne dönüştürüldü ve çeşitli nükleofillerle asit klorür arasında yeni türevlerin reaksiyonları gerçekleştirildi. Esterler (4a-c), ilgili alkoller ve asit klorür (3) ile Schotten Baumann metodu kullanılarak elde edildi. Pirazolopiridazinon türevleri (8, 9, 10), pirazol karboksilik asit ve çeşitli hidrazinler arasındaki halkalanma reaksiyonları sonucunda elde edildi. Ek olarak, amidleri (5a, 5b-5f) ve karbon-üre türevlerini (6a-c) elde etmek için asit klorür ile çeşitli aminler ve ürelerle reaksiyonlar gerçekleştirildi. Nitril bileşiği (7), SOCl2 ve DMF kullanılarak amin bileşiğinden suyun uzaklaştırılması ile elde edildi. Sentezlenen tüm moleküller, potansiyel aktivitelerinden dolayı antimikrobiyal aktiviteye tabi tutuldu. Moleküllerden 6-nitro-3,4-difenil-2-(4-(triflorometil)fenil)-2,6-dihidro-7Hpirazolo[3,4-d]piridazin-7-on bileşiğinin (10) sadece Gram-pozitif bakterilere karşı antibakteriyal aktivite gösterdi. Bacillus cereus ve Micrococcus luteus, A MIC değerleri 32 ve 128 µg/mL aktif olduğu bulundu. Yapısında nitro grubu bulunduran ve aktivite gösteren 10 nolu molekülden dolayı fonksiyonel grubun aktivite üzerinde önemli bir etkisi olduğu söylenebilir. Ayrıca 10 nolu molekülün pozitif kontrol olan streptomycin antibiyotiğinden daha etkili bir zon oluşturduğu da gözlendi. Bu durumda etkisini gösterdiği bakteriler için ileri çalışmalar konusunda iyi bir antibiyotik adayı olabilir.
Anahtar Kelime: Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
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| APA | Hacıalioğlu e, TASDEMIR V, genç h, TOZLU I (2019). Synthesis and Some Reactions of Pyrazole-3-carboxylic acid Having Trifluoromethyl Unit. , 645 - 654. 10.17714/gumusfenbil.528165 |
| Chicago | Hacıalioğlu elif,TASDEMIR VOLKAN,genç hasan,TOZLU ISRAFIL Synthesis and Some Reactions of Pyrazole-3-carboxylic acid Having Trifluoromethyl Unit. (2019): 645 - 654. 10.17714/gumusfenbil.528165 |
| MLA | Hacıalioğlu elif,TASDEMIR VOLKAN,genç hasan,TOZLU ISRAFIL Synthesis and Some Reactions of Pyrazole-3-carboxylic acid Having Trifluoromethyl Unit. , 2019, ss.645 - 654. 10.17714/gumusfenbil.528165 |
| AMA | Hacıalioğlu e,TASDEMIR V,genç h,TOZLU I Synthesis and Some Reactions of Pyrazole-3-carboxylic acid Having Trifluoromethyl Unit. . 2019; 645 - 654. 10.17714/gumusfenbil.528165 |
| Vancouver | Hacıalioğlu e,TASDEMIR V,genç h,TOZLU I Synthesis and Some Reactions of Pyrazole-3-carboxylic acid Having Trifluoromethyl Unit. . 2019; 645 - 654. 10.17714/gumusfenbil.528165 |
| IEEE | Hacıalioğlu e,TASDEMIR V,genç h,TOZLU I "Synthesis and Some Reactions of Pyrazole-3-carboxylic acid Having Trifluoromethyl Unit." , ss.645 - 654, 2019. 10.17714/gumusfenbil.528165 |
| ISNAD | Hacıalioğlu, elif vd. "Synthesis and Some Reactions of Pyrazole-3-carboxylic acid Having Trifluoromethyl Unit". (2019), 645-654. https://doi.org/10.17714/gumusfenbil.528165 |
| APA | Hacıalioğlu e, TASDEMIR V, genç h, TOZLU I (2019). Synthesis and Some Reactions of Pyrazole-3-carboxylic acid Having Trifluoromethyl Unit. Gümüşhane Üniversitesi Fen Bilimleri Dergisi, 9(4), 645 - 654. 10.17714/gumusfenbil.528165 |
| Chicago | Hacıalioğlu elif,TASDEMIR VOLKAN,genç hasan,TOZLU ISRAFIL Synthesis and Some Reactions of Pyrazole-3-carboxylic acid Having Trifluoromethyl Unit. Gümüşhane Üniversitesi Fen Bilimleri Dergisi 9, no.4 (2019): 645 - 654. 10.17714/gumusfenbil.528165 |
| MLA | Hacıalioğlu elif,TASDEMIR VOLKAN,genç hasan,TOZLU ISRAFIL Synthesis and Some Reactions of Pyrazole-3-carboxylic acid Having Trifluoromethyl Unit. Gümüşhane Üniversitesi Fen Bilimleri Dergisi, vol.9, no.4, 2019, ss.645 - 654. 10.17714/gumusfenbil.528165 |
| AMA | Hacıalioğlu e,TASDEMIR V,genç h,TOZLU I Synthesis and Some Reactions of Pyrazole-3-carboxylic acid Having Trifluoromethyl Unit. Gümüşhane Üniversitesi Fen Bilimleri Dergisi. 2019; 9(4): 645 - 654. 10.17714/gumusfenbil.528165 |
| Vancouver | Hacıalioğlu e,TASDEMIR V,genç h,TOZLU I Synthesis and Some Reactions of Pyrazole-3-carboxylic acid Having Trifluoromethyl Unit. Gümüşhane Üniversitesi Fen Bilimleri Dergisi. 2019; 9(4): 645 - 654. 10.17714/gumusfenbil.528165 |
| IEEE | Hacıalioğlu e,TASDEMIR V,genç h,TOZLU I "Synthesis and Some Reactions of Pyrazole-3-carboxylic acid Having Trifluoromethyl Unit." Gümüşhane Üniversitesi Fen Bilimleri Dergisi, 9, ss.645 - 654, 2019. 10.17714/gumusfenbil.528165 |
| ISNAD | Hacıalioğlu, elif vd. "Synthesis and Some Reactions of Pyrazole-3-carboxylic acid Having Trifluoromethyl Unit". Gümüşhane Üniversitesi Fen Bilimleri Dergisi 9/4 (2019), 645-654. https://doi.org/10.17714/gumusfenbil.528165 |
