Citation:
Chao Wu, Zhi-Wu Liang, Ying-Ying Xu, Wei-Min He, Jian-Nan Xiang. Gold-catalyzed oxazoles synthesis and their relevant antiproliferative activities[J]. Chinese Chemical Letters,
;2013, 24(12): 1064-1066.
-
Nine 5-aryl-2-methyloxazole derivatives were synthesized via gold-catalyzed alkyne oxidation. All of the compounds have been screened for their antiproliferative activities against MCF-7 cell (human breast carcinoma), A549 cell (human lung carcinoma) and Hela cell (human cervical carcinoma) lines in vitro. The results revealed that compounds 1b,1c and 1d exhibited strong inhibitory activities against the MCF-7 cell lines (with IC50 values of 4.6, 9.7 and 2.2 μmol/L, respectively).
-
Keywords:
- Oxazole,
- Synthesis,
- Gold-catalyzed,
- Biological activity
-
-
-
[1]
[1] (a) D. Kumar, M. Kumar, K.H. Chang, et al., An expeditious synthesis and anticancer activity of novel 4-(3'-indolyl)oxazoles, Eur. J. Med. Chem. 45 (2010) 1244- 1249;
-
[2]
(b) Z. Jin, Muscarine, imidazole, oxazole, and thiazole alkaloids, Nat. Prod. Rep. 28 (2011) 1143-1191;
-
[3]
(c) V.S.C. Yeh, Recent advances in the total syntheses of oxazole-containing natural products, Tetrahedron 60 (2004) 11995-12042;
-
[4]
(d) B. Wang, T. Hansen, T. Wang, et al., Total synthesis of phorboxazole A via de novo oxazole formation: strategy and component assembly, J. Am. Chem. Soc. 133 (2011) 1484-1505.
-
[5]
[2] (a) R. Misra, H.Y. Xiao, K. Kim, et al., N-(cycloalkylamino)acyl-2-aminothiazole inhibitors of cyclin-dependent kinase 2. N-[5-[[[5-(1,1-dimethylethyl)-2-oxazolyl] methyl]thio]-2-thiazolyl]-4-piperidinecarboxamide (BMS-387032), a highly efficacious and selective antitumor agent, J. Med. Chem. 47 (2004) 1719-1728;
-
[6]
(b) Y. Koyama, K. Yokose, L. Dolby, et al., Isolation, characterization and synthesis of pimprinine, pimprinethine and pimprinaphine, metabolites of Streptoverticillium olivoreticuli, Agric. Biol. Chem. 45 (1981) 1285-1287.
-
[7]
[3] A.O.D. Souza, M.T.C. Pedrosa, J.B. Alderete, et al., Cytotoxicity, antitumoral and antimycobacterial activity of tetrazole and oxadiazole derivatives, Pharmazie 60 (2005) 396-397.
-
[8]
[4] K. Atul, A. Pervez, M.A. Ram, et al., Novel 2-aryl-naphtho[1,2-d]oxazole derivatives as potential PTP-1B inhibitors showing antihyperglycemic activities, Eur. J. Med. Chem. 44 (2009) 109-116.
-
[9]
[5] L.S. Boulos, M.H.N. Arsanious, E.F. Ewies, Studies on phosphonium Ylides XXV: the behavior of active phosphacumulene and stabilized alkylidenephosphoranes towards 5-(4H)-oxazolones, Phosphorus Sulfur Silicon Relat. Elem. 184 (2009) 275-290.
-
[10]
[6] M. Natesan, Z. Gu, P. Stein, Biphenylsulfonamide endothelin receptor antagonists. 2. Discovery of 4'-oxazolyl biphenylsulfonamides as a new class of potent, highly selective ETA antagonists, J. Med. Chem. 43 (2000) 3111-3117.
-
[11]
[7] W.S. Yang, K. Shimada, D. Delva, et al., Identification of simple compounds with microtubule-binding activity that inhibit cancer cell growth with high potency, ACS Med. Chem. Lett. 3 (2012) 35-38.
-
[12]
[8] I. Cano, E. Álvarez, M.C. Nicasio, et al., Regioselective formation of 2,5-disubstituted oxazoles via copper(i)-catalyzed cycloaddition of acyl azides and 1-alkynes, J. Am. Chem. Soc. 133 (2011) 191-193.
-
[13]
[9] E.E. Wiegand, D.W. Rathburn, Polyphosphoric acid cyclization of acetamidoketones to 2,5-dimethyl-1,3-oxazoles, Synthesis 2 (1970) 648-649.
-
[14]
[10] (a) A.S.K. Hashmi, Gold-catalyzed organic reactions, Chem. Rev. 107 (2007) 3180-3211;
-
[15]
(b) A. Corma, A. Leyva-Perez, M. Sabater, et al., Gold-catalyzed carbon-heteroatom bond-forming reactions, Chem. Rev. 111 (2011) 1657-1712;
-
[16]
(c) A.S.K. Hashmi, C. Hubbert, Gold and organocatalysis combined, Angew. Chem. Int. Ed. 49 (2010) 1010-1012;
-
[17]
(d) B. Alcaide, P. Almendros, J. Alonso, Gold catalyzed oxycyclizations of alkynols and alkyndiols, Org. Biomol. Chem. 9 (2011) 4405-4416.
-
[18]
[11] (a) J. Xiao, X.W. Li, Gold a-oxo carbenoids in catalysis: catalytic oxygen-atom transfer to alkynes, Angew. Chem. Int. Ed. 50 (2011) 7226-7236;
-
[19]
(b) B. Lu, C.Q. Li, L.M. Zhang, Gold-catalyzed highly regioselective oxidation of C- C triple bonds without acid additives: propargyl moieties as masked a,b-unsaturated carbonyls, J. Am. Chem. Soc. 132 (2010) 14070-14072;
-
[20]
(c) L.W. Ye, W.M. He, L.M. Zhang, A flexible and stereoselective synthesis of azetidin-3-ones through gold-catalyzed intermolecular oxidation of alkynes, Angew. Chem. Int. Ed. 50 (2011) 3236-3239.
-
[21]
[12] W.M. He, C.Q. Li, L.M. Zhang, An efficient [2 + 2 + 1] synthesis of 2,5-disubstituted oxazoles via gold-catalyzed intermolecular alkyne oxidation, J. Am. Chem. Soc. 133 (2011) 8482-8485.
-
[22]
[13] (a) T. Sakamoto, M. Shiraiwa, Y. Konodo, et al., A facile synthesis of ethynylsubstituted six-membered n-heteroaromatic compounds, Synthesis (1983) 312- 314;
-
[23]
(b) A. Gangjee, J. Yu, R. Kisliuk, 2-Amino-4-oxo-6-substituted-pyrrolo[2,3-d]pynmidines as potential inhibitors of thymidylate synthase, J. Heterocyclic Chem. 39 (2002) 833-840;
-
[24]
(c) J.J. Qi, C.H. Tung, Development of benzothiazole ‘click-on' fluorogenic dyes, Bioorg. Med. Chem. Lett. 21 (2011) 320-323.
-
[25]
[14] (a) M. Rosenblum, N. Brawn, J. Papenmeier, et al., Synthesis of ferrocenylacetylenes, J. Organometal. Chem. 6 (1966) 173-180;
-
[26]
(b) A. Aguilar, A. Allen, E. Cabrera, et al., Ferrocenylketene and ferrocenyl-1,2- bisketenes: δirect observation and reactivity measurements, J. Org. Chem. 70 (2005) 9556-9561.
-
[27]
[15] Spectroscopic data: 1a: 1H NMR (400 MHz, CDCl3): δ 2.52 (s, 3H), 7.20 (s, 1H), 7.30 (t, 1H, J = 7.6 Hz), 7.40 (t, 2H, J = 7.6 Hz), 7.60 (d, 2H, J = 7.2 Hz). HRMS-EI: [M+] Calcd. for C10H9NO 159.0679, Found 159.0680. 1b: 1H NMR (400 MHz, CDCl3): δ 2.58 (s, 3H), 7.33 (s, 1H), 7.49 (m, 2H), 7.66 (d, 1H, J = 7.2 Hz), 7.72 (d, 2H, J = 7.2 Hz), 7.87 (d, 1H, J = 7.6 Hz), 8.09 (s, 1H). HRMS-EI: [M+] Calcd. for C14H11NO 209.0836, Found 209.0838. 1c: 1H NMR (400 MHz, CDCl3): δ 2.55 (s, 3H), 7.30 (s, 1H), 7.32-7.36 (m, 1H), 7.87 (d, 1H, J = 8.0 Hz), 8.53 (d, 1H, J = 6.8 Hz), 8.87 (s, 1H). HRMS-EI: [M+] Calcd. for C9H8N2O 160.0632, Found 160.0633. 1d: 1H NMR (400 MHz, CDCl3): δ 2.59 (s, 3H), 7.42 (s, 1H), 7.57 (t, 1H, J = 8.8 Hz), 7.671 (t, 1H, J = 8.2 Hz), 7.85 (d, 1H, J = 8.4 Hz), 8.10 (d, 1H, J = 8.4 Hz), 8.31 (s, 1H), 9.14 (s, 1H). HRMS-EI: [M+] Calcd. for C13H10N2O 210.0788, Found 210.0789. 1e: 1H NMR (400 MHz, CDCl3): δ 2.50 (s, 3H), 7.05 (s, 1H), 7.25-7.27 (m, 1H), 7.35-7.37 (m, 1H), 7.46-7.47 (m, 1H). HRMS-EI: [M+] Calcd. for C8H7NOS 165.0243, Found 165.0242. 1f: 1H NMR (400 MHz, CDCl3): δ 2.51 (s, 3H), 7.32 (s, 1H), 7.40-7.44 (m, 1H), 7.46-7.50 (m, 1H), 7.69 (s, 1H), 7.90 (d, 1H, J = 9.6 Hz), 8.05 (d, 1H, J = 8.0 Hz). HRMS-EI: [M+] Calcd. for C12H9NOS 215.0400, Found 215.0401. 1g: 1H NMR (400 MHz, CDCl3): δ 2.50 (s, 3H), 7.29 (s, 1H), 7.43-7.61 (m, 2H), 7.86 (d, 1H, J = 7.8 Hz), 8.03 (d, 1H, J = 7.4 Hz). HRMS-EI: [M+] Calcd. for C11H8N2OS 216.0352, Found 216.0351. 1h: 1HNMR(400 MHz, CDCl3): δ 2.48 (s, 3H), 4.12 (s, 5H), 4.30 (s, 2H), 4.56 (s, 2H), 6.82 (s, 1H). HRMS-EI: [M+] Calcd. for C14H13FeNO 267.0342, Found 267.0344. Procedure to synthesis of 1i: A solution of NaOH (1.0 mol/L, 3 mL) was added to a stirring solution of 2-methyl-5-(1-tosyl-1H-indol-3-yl)oxazole 6 (106 mg, 0.3 mmol) in 5 mL of methanol and heated to reflux at 80℃ under nitrogen overnight until starting material was consumed as monitored by TLC. Methanol was removed in vacuo and product was extracted with ether (3×20 mL), washed with brine, dried over magnesium sulfate, and concentrated in vacuo to give 56 mg (95% yield) of a yellow solid. 1H NMR (400 MHz, CDCl3): δ 2.58 (s, 3H), 7.16 (s, 1H), 7.22-7.32 (m, 2H), 7.46 (d, 1H, J = 7.6 Hz), 7.52 (d, 1H, J = 7.6 Hz), 7.78 (d, 1H, J = 8.0 Hz), 8.38 (s, 1H). HRMS-EI: [M+] Calcd. for C12H10N2O 198.0788, Found 198.0790.
-
[28]
[16] D.J. Gorin, B.D. Sherry, F.D. Toste, Ligand effects in homogeneous Au catalysis, Chem. Rev. 108 (2008) 3351-3378.
-
[29]
[17] (a) M. Patra, G. Gasser, N. Metzler-Nolte, Small organometallic compounds as antibacterial agents, Dalton Trans. 41 (2012) 6350-6358;
-
[30]
(b) R.D. Miao, J. Wei, M.H. Lv, et al., Conjugation of substituted ferrocenyl to thiadiazine as apoptosis-inducing agents targeting the Bax/Bcl-2 pathway, Eur. J. Med. Chem. 46 (2011) 5000-5009;
-
[31]
(c) B.H. Long, C.L. He, Y.B. Yang, et al., Synthesis, characterization and antibacterial activities of some new ferrocene-containing penems, Eur. J. Med. Chem. 45 (2010) 1181-1188;
-
[32]
(d) B.H. Long, S.Z. Liang, D.C. Xin, et al., Synthesis, characterization and in vitro antiproliferative activities of new 13-cis-retinoyl ferrocene derivatives, Eur. J. Med. Chem. 44 (2009) 2572-2576;
-
[33]
(e) S.L. Shen, J. Zhu, M. Li, et al., Synthesis of ferrocenyl pyrazole-containing chiral aminoethanol derivatives and their inhibition against A549 and H322 lung cancer cells, Eur. J. Med. Chem. 54 (2012) 287-294.
-
[1]
-
-
-
[1]
Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
-
[2]
Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp3)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
-
[3]
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
-
[4]
Huiju Cao , Lei Shi . sp1-Hybridized linear and cyclic carbon chain. Chinese Chemical Letters, 2025, 36(4): 110466-. doi: 10.1016/j.cclet.2024.110466
-
[5]
Ping Sun , Yuanqin Huang , Shunhong Chen , Xining Ma , Zhaokai Yang , Jian Wu . Indole derivatives as agrochemicals: An overview. Chinese Chemical Letters, 2024, 35(7): 109005-. doi: 10.1016/j.cclet.2023.109005
-
[6]
Wei Sun , Anjing Liao , Li Lei , Xu Tang , Ya Wang , Jian Wu . Research progress on piperidine-containing compounds as agrochemicals. Chinese Chemical Letters, 2025, 36(1): 109855-. doi: 10.1016/j.cclet.2024.109855
-
[7]
Anjing Liao , Wei Sun , Yaming Liu , Han Yan , Zhi Xia , Jian Wu . Pyrrole and pyrrolidine analogs: The promising scaffold in discovery of pesticides. Chinese Chemical Letters, 2025, 36(3): 110094-. doi: 10.1016/j.cclet.2024.110094
-
[8]
Ali Dai , Zhiguo Zheng , Liusheng Duan , Jian Wu , Weiming Tan . Small molecule chemical scaffolds in plant growth regulators for the development of agrochemicals. Chinese Chemical Letters, 2025, 36(4): 110462-. doi: 10.1016/j.cclet.2024.110462
-
[9]
Chong-Yang Shi , Jian-Xing Gong , Zhen Li , Chao Shu , Long-Wu Ye , Qing Sun , Bo Zhou , Xin-Qi Zhu . Gold-catalyzed intermolecular amination of allyl azides with ynamides: Efficient construction of 3-azabicyclo[3.1.0] scaffold. Chinese Chemical Letters, 2025, 36(2): 109895-. doi: 10.1016/j.cclet.2024.109895
-
[10]
Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
-
[11]
Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
-
[12]
Yanye Fan , Jingjing Chen , Bichun Chen , Jinyu Bai , Bowen Yang , Feng Liang , Lijing Fang . Design, synthesis and biological evaluation of Leu10-teixobactin analogues. Chinese Chemical Letters, 2025, 36(4): 110075-. doi: 10.1016/j.cclet.2024.110075
-
[13]
Mianling Yang , Meehyein Kim , Peng Zhan . Modular miniaturized synthesis and in situ biological evaluation facilitate rapid discovery of potent MraY inhibitors as antibacterial agents. Chinese Chemical Letters, 2025, 36(2): 110455-. doi: 10.1016/j.cclet.2024.110455
-
[14]
Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
-
[15]
Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
-
[16]
Long Jin , Jian Han , Dongmei Fang , Min Wang , Jian Liao . Pd-catalyzed asymmetric carbonyl alkynylation: Synthesis of axial chiral ynones. Chinese Chemical Letters, 2024, 35(6): 109212-. doi: 10.1016/j.cclet.2023.109212
-
[17]
Minjun Yin , Yuhui Lin , Manli Zhuang , Wei Xiao , Jie Wu . Photoredox-catalyzed synthesis of α,α-difluoromethyl-β-alkoxysulfones from sulfur dioxide. Chinese Chemical Letters, 2025, 36(3): 109926-. doi: 10.1016/j.cclet.2024.109926
-
[18]
Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
-
[19]
Guoping Yang , Zhoufu Lin , Xize Zhang , Jiawei Cao , Xuejiao Chen , Yufeng Liu , Xiaoling Lin , Ke Li . Assembly of Y(Ⅲ)-containing antimonotungstates induced by malic acid with catalytic activity for the synthesis of imidazoles. Chinese Chemical Letters, 2024, 35(12): 110274-. doi: 10.1016/j.cclet.2024.110274
-
[20]
Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(677)
- HTML views(30)