Advances in synthesis and biological activities of benzotriazole analogues: A micro review

被引:18
作者
Bollikolla, Hari Babu [1 ]
Boddapati, S. N. Murthy [1 ,2 ,3 ]
Thangamani, Swetha [4 ]
Mutchu, Baby Ramana [1 ]
Alam, Mohammed Mujahid [5 ]
Hussien, Mohamed [5 ,6 ]
Jonnalagadda, Sreekantha Babu [3 ]
机构
[1] Acharya Nagarjuna Univ, Dept Chem, Guntur 522510, Andhra Pradesh, India
[2] Sir CR Reddy Coll, Dept Chem, Eluru, Andhra Pradesh, India
[3] Univ KwaZulu Natal, Sch Chem & Phys, Westville Campus, Durban, South Africa
[4] Erode Arts & Sci Coll A, Dept Chem, Erode, Tamil Nadu, India
[5] King Khalid Univ, Coll Sci, Dept Chem, Abha, Saudi Arabia
[6] Agr Res Ctr, Dept Pesticide Formulat, Giza, Egypt
关键词
AMINATION REGIOSELECTIVE SYNTHESIS; BENZYNE CLICK CHEMISTRY; C-H ACTIVATION; IN-VITRO; INTRAMOLECULAR CYCLIZATION; 1,3-DIPOLAR CYCLOADDITION; 1,7-PALLADIUM MIGRATION; MODULAR SYNTHESIS; DERIVATIVES; INHIBITORS;
D O I
10.1002/jhet.4587
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Although the first synthesis of benzotriazole was performed in the 19th century still new methods for their preparation have developed. In this micro review authors focus mostly on the various synthetic strategies developed so far to synthesize benzotriazole and its derivatives by different strategies, such as metal-free, metal-assisted [3 + 2] cycloaddition reactions, cyclocondensations, flow methods, heterocyclizations, and so forth. This micro review combines recent (2005-2022 till date) information on the strategies used for the synthesis of benzotriazoles. Moreover, a brief overview of the bio applications of the benzotriazole scaffold along with pharmacological activity is also discussed.
引用
收藏
页码:705 / 742
页数:38
相关论文
共 112 条
[1]   Making endo-cyclizations favorable again: a conceptually new synthetic approach to benzotriazoles via azide group directed lithiation/cyclization of 2-azidoaryl bromides [J].
Ageshina, Alexandra A. ;
Chesnokov, Gleb A. ;
Topchiy, Maxim A. ;
Alabugin, Igor V. ;
Nechaev, Mikhail S. ;
Asachenko, Andrey F. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (18) :4523-4534
[2]   Synthesis, characterization, and biological activity of N1-methyl-2-(1H-1,2,3-benzotriazol-1-y1)-3-oxobutanethioamide complexes with some divalent metal (II) ions [J].
Al-Awadi, Nouria A. ;
Shuaib, Nadia M. ;
Abbas, Alaa ;
El-Sherif, Ahmed A. ;
El-Dissouky, Ali ;
Al-Saleh, Esmaeil .
BIOINORGANIC CHEMISTRY AND APPLICATIONS, 2008, 2008
[3]   Benzotriazoles in the Aquatic Environment: a Review of Their Occurrence, Toxicity, Degradation and Analysis [J].
Alotaibi, M. D. ;
McKinley, A. J. ;
Patterson, B. M. ;
Reeder, A. Y. .
WATER AIR AND SOIL POLLUTION, 2015, 226 (07)
[4]   tert-Butyl nitrite mediated nitrogen transfer reactions: synthesis of benzotriazoles and azides at room temperature [J].
Azeez, Sadaf ;
Chaudhary, Priyanka ;
Sureshbabu, Popuri ;
Sabiah, Shahulhameed ;
Kandasamy, Jeyakumar .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (37) :8280-8285
[5]   Similarity analysis, synthesis, and bioassay of antibacterial cyclic peptidomimetics [J].
Berhanu, Workalemahu M. ;
Ibrahim, Mohamed A. ;
Pillai, Girinath G. ;
Oliferenko, Alexander A. ;
Khelashvili, Levan ;
Jabeen, Farukh ;
Mirza, Bushra ;
Ansari, Farzana Latif ;
ul-Haq, Ihsan ;
El-Feky, Said A. ;
Katritzky, Alan R. .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 :1146-1160
[6]   Crystal and electronic structure of stable nitrenium ions. A comparison with structurally related carbenes [J].
Boche, G ;
Andrews, P ;
Harms, K ;
Marsch, M ;
Rangappa, KS ;
Schimeczek, M ;
Willeke, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (21) :4925-4930
[7]   1-(5-Carboxyindol-1-yl)propan-2-ones as inhibitors of human cytosolic phospholipase A2α: Synthesis and properties of bioisosteric benzimidazole, benzotriazole and indazole analogues [J].
Bovens, Stefanie ;
Kaptur, Martina ;
Elfringhoff, Alwine Schulze ;
Lehr, Matthias .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (08) :2107-2111
[8]   Benzotriazole: An overview on its versatile biological behavior [J].
Briguglio, I. ;
Piras, S. ;
Corona, P. ;
Gavini, E. ;
Nieddu, M. ;
Boatto, G. ;
Carta, A. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 97 :612-648
[9]   Design and preparation of new palladium precatalysts for C-C and C-N cross-coupling reactions [J].
Bruno, Nicholas C. ;
Tudge, Matthew T. ;
Buchwald, Stephen L. .
CHEMICAL SCIENCE, 2013, 4 (03) :916-920
[10]   SYNTHESIS AND TRAZODONE-LIKE PHARMACOLOGICAL PROFILE OF 1- AND 2-[3-[4-(X)-1-PIPERAZINYL]-PROPYL]BENZOTRIAZOLES [J].
CALIENDO, G ;
DICARLO, R ;
MELI, R ;
PERISSUTTI, E ;
SANTAGADA, V ;
SILIPO, C ;
VITTORIA, A .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1993, 28 (12) :969-974