BENZOTRIAZOLE DERIVATE (BENZOTRAZOL TREVLER)
BENZOTRIAZOLE DERIVATE
CAS No: 95-14-7
EINECS No: 202-394-1
CAS: 1-(1H-benzo[d][1,2,3]triazole-1-carbonyl)-3,5-diphenylformazan; 1-(1H-benzo[d][1,2,3]triazole-1-carbonyl)-5-(4-nitrophenyl)-3-phenyl formazan (5B); 1-(1H-benzo[d][1,2,3]triazole-1-carbonyl)-5-(4-chlorophenyl)-3-(furan-2-yl) formazan (5G); 1-(1H-benzo[d][1,2,3]triazole-1-carbonyl)-5-(4-bromophenyl)-3-(furan-2-yl) formazan (5H); 1-(1H-benzo[d][1,2,3]triazole-1-carbonyl)-3-(4-chlorophenyl)-5-phenyl formazan (5M); 1-(1H-benzo[d][1,2,3]triazole-1-carbonyl)-3,5-bis(4-chloro- phenyl) formazan (5O);M12761-(Methoxymethyl)-1H-benzotriazole; B19031H-Benzotriazole-1-methanol; C15261-(Chloromethyl)-1H-benzotriazole; 1,2,3-Benzotriazole, BtaH, 1,2,3-1H-Benzotriazole, 1,2,3-Benzotriazole, 1,2,3-Triaza-1H-indene, 1,2,3-Triazaindene, 1,2-AMINOAZOPHENYLENE, 1H-1,2,3-Benzotriazole
1H-Benzotraizole, 1H-BENZOTRIAZOL, 1H-Benzotriazole, 2,3-Diazaindole, Azimidobenzene, Aziminobenzene, Benzene, azimide, Benzisotriazole, Benzotriazol, Benzotriazole, BLS 1326, BT 120, BT 120 (lubricant additive), BTA, BTA (corrosion inhibitor), C.V.I. Liquid, Cobratec 35G, Cobratec 99, CVI, D 32-108, Entek, Irgastab I 489, ISK 3, Kemitec TT, M 318, NSC 3058, Rusmin R, Seetec BT, Seetec BT-R, Verzone Crystal, 1,2,3-1H-Benzotriazole, 1,2,3-Benzotriazole, 1,2,3-triaza-1H-indene, 1,2,3-triazaindene, 1H-1,2,3-Benzotriazole , 1H-benzo[1,2,3]triazole, 1H-Benzo[d][1,2,3]triazole, 1H-Benzotriazol , 1H-Benzotriazole , 1H-Benzotriazole, 4-26-00-00093, 95-14-7 [RN], Benzotriazol, BTA, T56 BMNNJ [WLN], 116421-31-9 [RN], 25377-81-5 [RN], 27556-51-0 [RN], 28880-01-5 [RN], 70644-74-5 [RN], 94160-69-7 [RN], 1,2,3-Benztriazole, 1,2-aminoazophenylene, 1,2-Aminozophenylene, 112133 [Beilstein], 2,3-diazaindole, azabenzimidazole, azaindazole, Azimidobenzene, aziminobenzene, benzene azimide, Benzisotriazole, benzo[1,2,3]triazole, benzo[d][1,2,3]triazole, Benzotriazole (VAN), Benztriazole, C012771, Cobratec #99, Cobratec 35G, Cobratec No. 99, Cobtratec 99, D 32-108, DM1225000 [RTECS], Drometrizole, Entek, Irgastab I 489, ISK 3, Pseudoazimidobenzene, titaniumisopropyloxide, UNII-86110UXM5Y, WLN: T56 BMNNJ
Antibacterial activity of some newer 1,2,3 – benzotriazole derivatives synthesized by ultrasonication in solvent – free conditions
INTRODUCTION
Heterocyclic compounds containing nitrogen atoms are considered to be one of the most effective antimicrobial drugs used as either single agents or in combination for cancer therapy . Some benzotriazole derivatives have shown antiinflammatory
properties . Touami et al reported that the conjugates of benzotriazole derivative photonucleases and DNA minor groove binders exhibit enhanced cleavage efficiency and unique selectivity. It has been proposed that the benzotriazole derivatives have the effect on cancer development . Sparatore and Sparatore reported that 2-(4-(Dialkyl amino alkoxy) phenyl) benzotriazoles and N-oxides works as thromboxane A2 antagonists and as hypocholesterolemic agents, platelet aggregation inhibitors , where as benzotriazole carboxylic acid or ester derivatives were found to be effective in the treatment of metabolic related disorders including atherosclerosis, coronary heart disease and type 2 diabetes . Biagi et al. reported that 5- (substituted) benzotriazoles and triazolyl benzotriazoles as potential potassium channel activators.
The ultrasound irradiation technique has been increasingly used in organic synthesis for last three decades. A large number of organic reactions have been carried out in higher yield, shorter reaction time and milder condition under ultrasound irradiation . It is well known that ultrasonic irradiation to a liquid phase reaction accelerates the chemical reaction and creates a special reaction field for the preparation of various materials . There is a growing awareness that the design of synthetic or chemical processes should follow the basic principles of green chemistry to reduce risks to humans and the environment. Largescale use of organic solvents in synthesis causes environmental hazards . There were several advantages of performing syntheses in solvent-free media, such as, short reaction time, increased safety, and low cost . Recently, a few papers reported modern synthetic protocols where solvent-less condition have been used . Finally, herein we wish to report the anti-bacterial activity of some newer 1,2,3 – benzotriazole derivatives synthesized by ultrasonication in solvent – free conditions.
Benzotriazole (BTA) is a heterocyclic compound containing three nitrogen atoms, with the chemical formula C6H5N3. This aromatic compound is colorless and polar and can be used in various fields.
Applications
Benzotriazole has been known for its great versatility. It has already been used as a restrainer in photographic emulsions and as a reagent for the analytical determination of silver. More importantly, it has been extensively used as a corrosion inhibitor in the atmosphere and underwater. Also, its derivatives and their effectiveness as drug precursors have been drawing attention. Besides all the application mentioned above, the BTA can be used as antifreezes, heating and cooling systems, hydraulic fluids and vapor phase inhibitors as well.
Corrosion inhibitor
Benzotriazole is an effective corrosion inhibitor for copper and its alloys by preventing undesirable surface reactions. It is known that a passive layer, consisting of a complex between copper and benzotriazole, is formed when copper is immersed in a solution containing benzotriazole. The passive layer is insoluble in aqueous and many organic solutions. There is a positive correlation between the thickness of the passive layer and the efficiency of preventing corrosion. BTA is used in conservation, notably for the treatment of bronze disease. The exact structure of the copper-BTA complex is controversial and many proposals have been suggested.
Drug precursor
Benzotriazole derivatives have chemical and biological properties that are versatile in the pharmaceutical industry. Benzotriazole derivatives act as agonists for many proteins. For instance, vorozole and alizapride have useful inhibitory properties against different proteins and benzotriazole esters have been reported to work as mechanism-based inactivators for severe acute respiratory syndrome (SARS) 3CL protease. The methodology is not only limited to heterocyclization but was also successful for polynuclear hydrocarbons of small carbocyclic systems.
Trazolopride & Tribendilol are other benztriazole examples of drugs.
Considering the need for discovery of new antifungal drugs with greater potency and broader spectrum of activity, a new series of 5-substituted benzotriazole derivatives were designed, through structure based design, as inhibitors of fungal cytochrome P450 lanosterol 14-α demethylase. These were further optimized by a combination of iterative medicinal chemistry principles and molecular docking. Based on the best docking scores, some benzotriazole derivatives were synthesized and characterized by IR, (1)H NMR and MS/MS. The molecules were evaluated for their antifungal action against Candida albicans by cup plate method and ergosterol quantification method by UV spectroscopy. Reasonably good correlation between docking scores and antifungal activity were observed. The computational predictions were in consensus with the experimental results.
Çözücü olmayan koullarda ultrason ile sentezlenen baz yeni 1,2,3 – benzotriazol türevlerinin antibakteriyel aktivitesi
GR
Azot atomlar içeren heterosiklik bileikler, tekli ajanlar olarak veya kanser terapisi için kombinasyon halinde kullanlan en etkili antimikrobiyal ilaçlardan biri olarak düünülür. Baz benzotriazol türevleri antiinflamatuar
özellikleri . Touami ve arkadalar, benzotriazol türevi fotonükleazlarn ve DNA küçük yivli balayclarn konjügatlarnn arttrlm bölünme verimi ve esiz seçicilii sergilediini bildirmitir. Benzotriazol türevlerinin kanser geliimini etkiledii önerilmitir. Sparatore ve Sparatore, 2- (4- (Dialkil amino alkoksi) fenil) benzotriazollerin ve N-oksitlerin, tromboksan A2 antagonistleri ve hipokolesterolemik ajanlar, trombosit agregasyon inhibitörleri olarak çaltn ve burada benzotriazol karboksilik asit veya ester türevlerinin etkili olduu bulunmutur Ateroskleroz, koroner kalp hastal ve tip 2 diyabet gibi metabolik hastalklarn tedavisi. Biagi ve ark. Potansiyel potasyum kanal etkinletiricileri olarak 5- (ikame edilmi) benzotriazollerin ve triazolil benzotriazollerin rapor edildi.
Ultrason nlama teknii son otuz yldr organik sentezde giderek daha fazla kullanlmaktadr. Çok sayda organik reaksiyon, daha yüksek verim, daha ksa reaksiyon süresi ve daha yumuak koullarda ultrason nlamas altnda gerçekletirildi. Bir sv faz reaksiyonuna ultrasonik radyasyonun kimyasal reaksiyonu hzlandrd ve çeitli materyallerin hazrlanmas için özel bir reaksiyon alan oluturduu bilinmektedir. nsanlara ve çevreye verilen riskleri azaltmak için sentetik veya kimyasal süreçlerin tasarmnn yeil kimyann temel prensiplerini takip etmesi gerektiinin farkndal giderek artmaktadr. Sentezde organik çözücülerin büyük ölçekli kullanm çevresel tehlikelere neden olur. Çözücü içermeyen ortamlarda, ksa tepki süresi, artan güvenlik ve düük maliyet gibi sentezlerin yaplmasnn birçok avantaj vard. Son zamanlarda, birkaç bildiri, solvent içermeyen koullarn kullanld modern sentetik protokoller bildirdi. Son olarak, burada, çözücü içermeyen koullarda ultrason ile sentezlenen baz yeni 1,2,3-benzotriazol türevlerinin anti-bakteriyel etkinliini bildirmek istiyoruz.
Benzotriazol (BTA), C6H5N3 kimyasal formülü ile üç nitrojen atomu içeren heterosiklik bir bileiktir. Bu aromatik bileik renksiz ve polar olup çeitli alanlarda kullanlabilir.
Uygulamalar
Benzotriazol, çok yönlülüü ile biliniyor. Zaten fotorafik emülsiyonlarda bir snrlayc olarak ve gümüün analitik tayini için bir reaktif olarak kullanlmtr. Daha da önemlisi, atmosferde ve su altnda bir korozyon inhibitörü olarak yaygn ekilde kullanlmaktadr. Ayrca türevleri ve ilaç öncülleri olarak etkinlikleri de dikkat çekmektedir. Yukarda bahsedilen tüm uygulamalarn yannda BTA, antifriz, stma ve soutma sistemleri, hidrolik svlar ve buhar faz inhibitörleri olarak da kullanlabilir.
Paslanma önleyici
Benzotriazol, istenmeyen yüzey reaksiyonlarn önleyerek bakr ve alamlar için etkili bir korozyon inhibitörüdür. Bakr ve benzotriazol arasnda bir kompleksten oluan bir pasif tabakann bakrn benzotriazol içeren bir solüsyona batrlmas durumunda olutuu bilinmektedir. Pasif tabaka sulu ve birçok organik çözeltide çözünmez. Pasif tabaka kalnl ile korozyon önleme etkinlii arasnda pozitif bir iliki vardr. BTA, özellikle bronz hastalklarn tedavisinde korunmada kullanlr. Bakr-BTA kompleksinin tam yaps tartmaldr ve birçok öneri önerilmitir.
laç öncüsü
Benzotriazol türevleri, ilaç endüstrisinde çok yönlü olan kimyasal ve biyolojik özelliklere sahiptir. Benzotriazol türevleri birçok protein için agonist olarak etkindir. Örnein, vorozol ve alizaprid, farkl proteinlere kar yararl inhibitör özelliklere sahiptir ve benzotriazol esterlerin iddetli akut solunum yolu sendromu (SARS) 3CL proteaz için mekanizmaya dayal inaktivatörler olarak çalt bildirilmitir. Metodoloji yalnzca heterosiklizasyon ile snrl deildir, ayn zamanda küçük karbosiklik sistemlerin polinükleer hidrokarbonlar için de baarl olmutur.
Trazoloprid ve Tribendilol dier benztriazol ilaç örnekleri.
Daha fazla potens ve daha geni aktivite sergileyen yeni antifungal ilaçlarn kefi gereini göz önüne alarak, fungus sitokrom P450 lanosterol 14-α demetilazn önleyicileri olarak, yap temelli tasarm ile 5-ikame edilmi benzotriazol türevleri dizisi tasarland. Bunlar, tekrarlayc tbbi kimya ilkeleri ve moleküler yerletirme kombinasyonu ile daha da optimize edildi. En iyi yerletirme skorlarna dayanarak, baz benzotriazol türevleri IR, (1) H NMR ve MS / MS ile sentezlendi ve karakterize edildi. Moleküler, Candida albicans’a kar antifungal etki göstermesi için fincan plak yöntemi ve UV spektroskopisi ile ergosterol kantifikasyon yöntemi ile deerlendirildi. Doklama skorlar ile antifungal aktivite arasnda makul derecede iyi korelasyon gözlemlendi. Hesaplama tahminleri, deney sonuçlar ile konsensüs halindeydi.