Volkan TAŞDEMİR, Elif HACIALİOĞLU, Hasan GENÇ, İsrafil TOZLU

Synthesis and Some Reactions of Pyrazole-3-carboxylic acid Having Trifluoromethyl Unit

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 pyrazole carboxylic acid derivative was converted into acid chloride form. Reaction of new derivatives between acid chloride and some of nucleophiles were progressed. The esters (4a-c) were obtained using Schotten Baumann method with the corresponding alcohols and acid chloride (3). Pyrazolopiridazinone derivatives (8, 9, 10) were obtained as a result of cyclization reactions between pyrazole carboxylic acid and various hydrazines. Additionally, reactions between an acide chloride 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 of SOCl2 and DMF. All synthesized molecules were subjected to antibacterial activity to see their potential as unknown reagent. 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 a MIC value of 32 and 128 µg/mL, respectively. This finding revealed that functional group is important for antibacterial activity. Compound 10 having a nitro group inhibited growing of bacteria more than positive control, streptomycin in two different types of bacteria. This might be a good clue for further investigation about antibacterial agents.

Anahtar Kelimeler:

Cyclic oxalyl compounds, Cyclization, Fluoride, Pyrazole

Triflorometil Grubuna Sahip Pirazol-3-karboksilik Asit Sentezi ve Bazı Tepkimeleri

4-Benzoil-5-fenil-2,3-furandion 1 ve (4-(triflorometil)fenil) benzaldehit-fenil hidrazonun 1a reaksiyonundan 4-benzoil-5-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-7H-pirazolo[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.

Keywords:

Siklik okzalil bileşikleri, Halkalanma, Florür, Pirazol,

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