Citation:
E. Rajanarendar, K. Thirupathaiah, S. Ramakrishna, D. Nagaraju. A facile and convenient synthesis of novel imidazo[1,2-b] isoxazoles and their Mannich bases as potential biodynamic agents[J]. Chinese Chemical Letters,
;2015, 26(12): 1511-1513.
doi:
10.1016/j.cclet.2015.07.024
-
A series of novel imidazo[1,2-b]isoxazoles 3 and their Mannich bases 4-6 were synthesized via convenient reactions. The reaction of 3-aminoisoxazole 1 with substituted phenacyl bromides 2 in dry ethanol afforded the corresponding 6-methyl-3-aryl imidazo[1,2-b]isoxazoles 3 in good yields. Compounds 3 on treatment with 37% formaline and secondary amines furnished the corresponding novel Mannich bases viz., 6-methyl-3-aryl-2-(morpholine/pyrrolidin-1-yl/piperidin-1-yl)-methyl-imidazo[ 1,2-b]isoxazoles 4-6.
-
Keywords:
- Imidazo[1,2-b]isoxazoles
-
-
-
[1]
[1] E.M. Guantai, K. Ncokazi, T.J. Egan, et al., Design, synthesis and in vitro antimalarial evaluation of triazole-linked chalcone and dienone hybrid compounds, Bioorg. Med. Chem. 18 (2010) 8243-8256.
-
[2]
[2] C.A. Fraga, Drug hybridization strategies: before or after lead identification? Expert Opin. Drug Discov. 4 (2009) 605-609.
-
[3]
[3] F. Bellina, S. Cauteruccio, S. Montib, R. Rossi, Novel imidazole-based combretastatin A-4 analogues: Evaluation of their in vitro antitumor activity and molecular modelling study of their binding to the colchicines site of tubulin, Bioorg. Med. Chem. Lett. 16 (2006) 5757-5762.
-
[4]
[4] J.Z. Vlahakis, M. Humb, M.N. Rahman, et al., Synthesis and evaluation of imidazole- dioxolane compounds as selective heme oxygenase inhibitors: Effect of substituents at the 4-position of the dioxolane ring, Bioorg. Med. Chem. 17 (2009) 2461-2475.
-
[5]
[5] K. Bhandari, N. Srinivas, V.K. Marrapu, A. Verma, S. Srivastava, S. Gupta, Synthesis of substituted aryloxy alkyl and aryloxy aryl alkyl imidazoles as antileishmanial agents, Bioorg. Med. Chem. Lett. 20 (2010) 291-293.
-
[6]
[6] K. Hanazaki, P. Gupta, S.K. Singh, et al., Current antiviral therapy for chronic hepatitis C including liver transplantation and hepatic resection, Curr. Med. Chem. 2 (2003) 103-111.
-
[7]
[7] K. Bleicher, F. Gerber, Y. Wuthrich, A. Alanine, A. Capretta, Parallel synthesis of substituted imidazoles from 1,2-aminoalcohols, Tetrahedron Lett. 43 (2002) 7687-7690.
-
[8]
[8] (a) G. Trapani, M. Franco, A. Latrofa, et al., Derivatives of imidazole. III. Synthesis and pharmacological activities of nitriles, amides, and carboxylic acid derivatives of imidazo[[1,2-a] pyridines, J. Med. Chem. 42 (1999) 3934-3937; (b) G.J. George, D.P. Vercauteren, G.H. Evard, et al., Characterization of the physicchemical properties of the imidazopyridine derivative Alpidem, Comparison with Zolpidem, Eur. J. Med. Chem. 28 (1993) 323-325.
-
[9]
[9] S.M. Reilly, E.S. Newlands, M.G. Glaser, et al., Temozolomide: A new oral cytotoxic chemotherapeutic agent with promising activity against primary brain tumors, Eur. J. Cancer 29A (1993) 940-942.
-
[10]
[10] H.S. Friedman, T. Kerby, H. Calvert, Temozolomide and treatment of malignant glioma, Clin. Cancer Res. 6 (2000) 2585-2597.
-
[11]
[11] T. Batchelor, Primary nervous-system lymphoma, Lancet 355 (2000) 354-365.
-
[12]
[12] J. Getal, Synthesis of 3-[1,3-thazol-2-yl-] as potential antitumor agents, Antibiotics 28 (1975) 91-94.
-
[13]
[13] C.H. Eugster, Chemie der wirkstoffe aus dem fliegenpilz (amanita muscaria), Prog. Chem. Org. Nat. Prod. 27 (1969) 261.
-
[14]
[14] H. Kano, I. Adachi, R. Kido, K. Hirose VIII., Synthesis and pharmacological properties of 5-aminoalkyl- and 3-aminoalkylisoxazoles and related derivatives, J. Med. Chem. 10 (1967) 411-418.
-
[15]
[15] P.B. Reddy, S.M. Reddy, E. Rajanarendar, A.K. Murthy, Antifungal activity of isoxazolyl thiazolidin-4-ones, Indian Phytopathol. 37 (1984) 369-398.
-
[16]
[16] M.T. Chemicals, K.K. Mitsui, Seiyaku kogyoo, vol. 6, Toyama Chemical Co. Ltd., 1994p. 146.
-
[17]
[17] E.T. Marquis, J.R. Sanderson, US Patent 528335 (1994), Chem. Abstr. 120 (1994) 217649.
-
[18]
[18] Streling Drug. Inc., US Patent (1988) 4755595, Chem. Abstr. 110 (1989) 730.
-
[19]
[19] A. Sadanadam, M.V. Rajam, K. Subash, E. Rajanarendar, Production of chromosomal breaks by isoxazolyl thiazolidin-one in allium sativu, Indian Bot. Rep. 3 (1984) 38-42.
-
[20]
[20] F. Palagiano, L. Arenare, E. Luraschi, et al., Research on heterocyclic compounds XXXIV. Synthesis and SAR study of some imidazo[2,1-b] thiazole carboxylic and acetic acids with anti-inflammatory and analgesic activity, Eur. J. Med. Chem. 30 (1995) 901-909.
-
[21]
[21] S. Kamila, K. Mendoza, E.R. Biehl, Microwave-assisted Hantzsch thiazole synthesis of N-phenyl-4-16-phenylimidazo[2, 1-b] thiazole-5-yl)-thiazol-2-amines from the reaction of 2-chloro-1-(6-phenylimidazo[2,1-b]thiazole-5-yl)ethenones and thioureas, Tetrahedron Lett. 53 (2012) 4921-4924.
-
[22]
[22] (a) E. Rajanarendar, S. Ramakrishna, K. Ramamurthy, Synthesis of novel isoxazolyl bis-thiazolo[3,2-a]pyrimidines, Chin. Chem. Lett. 23 (2012) 899-902; (b) E. Rajanarendar, S. Ramakrishna, K. Govardhan Reddy, D. Nagaraju, Y.N. Reddy, A facile synthesis, anti-inflammatory and analgesic activity of isoxazolyl- 2,3-dihydrospiro [benzo[f]isoindole-1,3'-indoline]-2',4,9-triones, Bioorg. Med. Chem. Lett. 23 (2013) 3954-3958; (c) E. Rajanarendar, K. Govardhan Reddy, S. Rama Krishna, et al., Synthesis and in vitro and in vivo anticancer activity of novel 3-methyl-5H-isoxazolo[ 5'4;:5,6]pyrido[2,3-b]indoles, Bioorg. Med. Chem. Lett. 22 (2012) 6677-6680; (d) E. Rajanarendar, G. Mohan, E. Kalyan Rao, M. Srinivas, Palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of organo boronic acids with N-protected 4-iodophenyl alanine linked isoxazoles, Chin. Chem. Lett. 1 (2009) 1-4; (e) E. Rajanarendar, A. Siva Rami Reddy, S. Raju, S. Firoz Pasha, K. Govardhan Reddy, A fast and highly efficient protocol for reductive amination of aromatic aldehydes using NaBH4 and isoxazole amines in an ionic liquid medium, Chin. J. Chem. 29 (2011) 769-772.
-
[1]
-
-
-
[1]
You Zhou , Li-Sheng Wang , Shuang-Gui Lei , Bo-Cheng Tang , Zhi-Cheng Yu , Xing Li , Yan-Dong Wu , Kai-Lu Zheng , An-Xin Wu . I2-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations. Chinese Chemical Letters, 2025, 36(1): 109799-. doi: 10.1016/j.cclet.2024.109799
-
[2]
Jiao Chen , Zihan Zhang , Guojin Sun , Yudi Cheng , Aihua Wu , Zefan Wang , Wenwen Jiang , Fulin Chen , Xiuying Xie , Jianli Li . Benzo[4,5]imidazo[1,2-a]pyrimidine-based structure-inherent targeting fluorescent sensor for imaging lysosomal viscosity and diagnosis of lysosomal storage disorders. Chinese Chemical Letters, 2024, 35(11): 110050-. doi: 10.1016/j.cclet.2024.110050
-
[3]
Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
-
[4]
Zhaodong WANG . In situ synthesis, crystal structure, and magnetic characterization of a trinuclear copper complex based on a multi-substituted imidazo[1,5-a]pyrazine scaffold. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 597-604. doi: 10.11862/CJIC.20240268
-
[5]
Bofei JIA , Zhihao LIU , Zongyuan GAO , Shuai ZHOU , Mengxiang WU , Qian ZHANG , Xiamei ZHANG , Shuzhong CHEN , Xiaohan YANG , Yahong LI . Cu(Ⅱ) and Cu(Ⅰ) complexes based on derivatives of imidazo[1,5-a]pyridine: Synthesis, structures, in situ metal-ligand reactions, and catalytic activity. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 1020-1036. doi: 10.11862/CJIC.20240317
-
[6]
Xiaochun Liu , Gaoyan Chen , Xiaodong Yue , Chaoyue Wang , Xue-Xin Zhang , Xuecheng Ran , Yingxiao Zong , Junke Wang , Xicun Wang . A novel N-stable Co2P nano-catalyst for the synthesis of quinoxalines by annulation of alkynes and 1,2-diaminobenzenes. Chinese Chemical Letters, 2025, 36(8): 110707-. doi: 10.1016/j.cclet.2024.110707
-
[7]
Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
-
[8]
Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
-
[9]
Yuan Xiong , Lan-Hui Qin , Bei Zhao , Lei-Zhi Xu , Yu-Fan Fan , Tian Tian , Hai-Rong Zeng , Ting Liu , Jian Huang , Jian-Ming Sun , Zhen-Hao Tian , Guang-Bo Ge . Structure-based design and development of halogenated-naphthalimides as potent hCYP1B1 inhibitors for overcoming paclitaxel resistance. Chinese Chemical Letters, 2025, 36(11): 110812-. doi: 10.1016/j.cclet.2024.110812
-
[10]
Tianze Wang , Junyi Ren , Dongxiang Zhang , Huan Wang , Jianjun Du , Xin-Dong Jiang , Guiling Wang . Development of functional dye with redshifted absorption based on Knoevenagel condensation at 1-site in phenyl[b]-fused BODIPY. Chinese Chemical Letters, 2024, 35(6): 108862-. doi: 10.1016/j.cclet.2023.108862
-
[11]
Miao-Miao Chen , Min-Ling Zhang , Xiao Song , Jun Jiang , Xiaoqian Tang , Qi Zhang , Xiuhua Zhang , Peiwu Li . Smartphone-assisted electrochemiluminescence imaging test strips towards dual-signal visualized and sensitive monitoring of aflatoxin B1 in corn samples. Chinese Chemical Letters, 2025, 36(1): 109785-. doi: 10.1016/j.cclet.2024.109785
-
[12]
Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
-
[13]
Tengfei Xuan , Xinyu Zhang , Wei Han , Yidong Huang , Weiwu Ren . Total synthesis of (+)-taberdicatine B and (+)-tabernabovine B. Chinese Chemical Letters, 2025, 36(2): 109816-. doi: 10.1016/j.cclet.2024.109816
-
[14]
Zhenhao Wang , Yuliang Tang , Ruyu Li , Shuai Tian , Yu Tang , Dehai Li . Bioinspired synthesis of cochlearol B and ganocin A. Chinese Chemical Letters, 2024, 35(7): 109247-. doi: 10.1016/j.cclet.2023.109247
-
[15]
Kai Zhou , Ao Sun , Yuchao Wang , Hang Dong , Chenkai Bai , Yidian Mo , Xuyang Ding , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Semisynthesis of rare chondroitin sulfate B and T oligosaccharides. Chinese Chemical Letters, 2025, 36(9): 110783-. doi: 10.1016/j.cclet.2024.110783
-
[16]
Bing Xie , Qi Jiang , Fang Zhu , Yaoyao Lai , Yueming Zhao , Wei He , Pei Yang . Transdermal delivery of amphotericin B using deep eutectic solvents for antifungal therapy. Chinese Chemical Letters, 2025, 36(5): 110508-. doi: 10.1016/j.cclet.2024.110508
-
[17]
Chenxi Shang , Boxuan Lu , Chongbei Wu , Shuqing Zhou , Luyan Shi , Tayirjan Taylor Isimjan , Xiulin Yang . Inducing electronic rearrangement through Co3B-Mo2B5 catalysts: Efficient dual-function catalysis for NaBH4 hydrolysis and 4-nitrophenol reduction. Chinese Chemical Letters, 2025, 36(9): 111152-. doi: 10.1016/j.cclet.2025.111152
-
[18]
Jiao CHEN , Yi LI , Yi XIE , Dandan DIAO , Qiang XIAO . Vapor-phase transport of MFI nanosheets for the fabrication of ultrathin b-axis oriented zeolite membranes. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 507-514. doi: 10.11862/CJIC.20230403
-
[19]
Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C6F5)3/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
-
[20]
Jia-Li Xie , Tian-Jin Xie , Yu-Jie Luo , Kai Mao , Cheng-Zhi Huang , Yuan-Fang Li , Shu-Jun Zhen . Octopus-like DNA nanostructure coupled with graphene oxide enhanced fluorescence anisotropy for hepatitis B virus DNA detection. Chinese Chemical Letters, 2024, 35(6): 109137-. doi: 10.1016/j.cclet.2023.109137
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(1169)
- HTML views(50)
Login In
DownLoad: