Effi cient and mild cyclization procedures for the synthesis of novel 2-amino-4<i>H</i>-pyran derivatives with potential antitumor activity

Citation: Dao-Cai Wang, Yong-Mei Xie, Chen Fan, Shun Yao, Hang Song. Effi cient and mild cyclization procedures for the synthesis of novel 2-amino-4H-pyran derivatives with potential antitumor activity[J]. Chinese Chemical Letters, 2014, 25(7): 1011-1013. doi: 10.1016/j.cclet.2014.04.026 shu

Effi cient and mild cyclization procedures for the synthesis of novel 2-amino-4H-pyran derivatives with potential antitumor activity

通讯作者: Hang Song,

基金项目:

convenient route to construct more diverse pyran analog libraries. The antitumor activity of the synthesized compounds was evaluated in three human tumor cell lines, including human colon cancer (HCT116) (HCT116)

human cervical cancer (Hela) (Hela)

nonsmall cell lung cancer (H1975). (H1975)

摘要: A series of novel 2-amino-4H-pyran derivatives have been synthesized via a three-component reaction of a, β-unsaturated ketone derivatives, malononitrile, aldehydes in excellent yields, using DBU as a catalyst and ethanol as a cheap, safe, and environmentally benign solvent under mild conditions. Their antitumor activity was evaluated in three human tumor cell lines, including human colon cancer (HCT116), human cervical cancer (Hela), and non-small cell lung cancer (H1975).

关键词:

English

Effi cient and mild cyclization procedures for the synthesis of novel 2-amino-4H-pyran derivatives with potential antitumor activity

1.
a Department of Pharmaceutical and Biological Engineering, College of Chemical Engineering, Sichuan University, Chengdu 610065, China;
2.
b State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, China

Corresponding author: Hang Song,

Received Date: 11 March 2014

Abstract: A series of novel 2-amino-4H-pyran derivatives have been synthesized via a three-component reaction of a, β-unsaturated ketone derivatives, malononitrile, aldehydes in excellent yields, using DBU as a catalyst and ethanol as a cheap, safe, and environmentally benign solvent under mild conditions. Their antitumor activity was evaluated in three human tumor cell lines, including human colon cancer (HCT116), human cervical cancer (Hela), and non-small cell lung cancer (H1975).

Key words:

1. [1] N. Sultana, P.G. Waterman, 3-Monoterpenyl-2,4-deoxygenated quinoline alkaloids from the aerial parts of Halfordia kendack, Phytochemistry 58 (2001) 329-332.[1] N. Sultana, P.G. Waterman, 3-Monoterpenyl-2,4-deoxygenated quinoline alkaloids from the aerial parts of Halfordia kendack, Phytochemistry 58 (2001) 329-332.
2. [2] K. Nakashima, M. Oyama, T. Ito, et al., Melicodenines A and B, novel Diels-Alder type adducts isolated from Melicope denhamii, Tetrahedron Lett. 52 (2011) 4694-4696.[2] K. Nakashima, M. Oyama, T. Ito, et al., Melicodenines A and B, novel Diels-Alder type adducts isolated from Melicope denhamii, Tetrahedron Lett. 52 (2011) 4694-4696.
3. [3] K. Nakashima, M. Oyama, T. Ito, et al., Novel quinolinone alkaloids bearing a lignoid moiety and related constituents in the leaves of Melicope denhamii, Tetrahedron 68 (2012) 2421-2428.[3] K. Nakashima, M. Oyama, T. Ito, et al., Novel quinolinone alkaloids bearing a lignoid moiety and related constituents in the leaves of Melicope denhamii, Tetrahedron 68 (2012) 2421-2428.
4. [4] I.S. Chen, I.W. Tsai, C.M. Teng, et al., Pyranoquinoline alkaloids from Zanthoxylum simulans, Phytochemistry 46 (1997) 525-529.[4] I.S. Chen, I.W. Tsai, C.M. Teng, et al., Pyranoquinoline alkaloids from Zanthoxylum simulans, Phytochemistry 46 (1997) 525-529.
5. [5] M. Isaka, M. Tanticharoen, P. Kongsaeree, et al., Structures of cordypyridones A-D, antimalarial N-hydroxy-and N-methoxy-2-pyridones from the insect pathogenic fungus Cordyceps nipponica, J. Org. Chem. 66 (2001) 4803-4808.[5] M. Isaka, M. Tanticharoen, P. Kongsaeree, et al., Structures of cordypyridones A-D, antimalarial N-hydroxy-and N-methoxy-2-pyridones from the insect pathogenic fungus Cordyceps nipponica, J. Org. Chem. 66 (2001) 4803-4808.
6. [6] C.L. Cantrell, K.K. Schrader, L.K. Mamonov, et al., Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii, J. Agric. Food Chem. 53 (2005) 7741-7748.[6] C.L. Cantrell, K.K. Schrader, L.K. Mamonov, et al., Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii, J. Agric. Food Chem. 53 (2005) 7741-7748.
7. [7] A.U. Rahman, A. Khalid, N. Sultana, et al., New natural cholinesterase inhibiting and calcium channel blocking quinoline alkaloids, J. Enzyme Inhib. Med. Chem. 21 (2006) 703-710.[7] A.U. Rahman, A. Khalid, N. Sultana, et al., New natural cholinesterase inhibiting and calcium channel blocking quinoline alkaloids, J. Enzyme Inhib. Med. Chem. 21 (2006) 703-710.
8. [8] P.L. Katavic, D.A. Venables, G.P. Guymer, et al., Alkaloids with human delta-opioid receptor binding affinity from the Australian rainforest tree Peripentadenia mearsii, J. Nat. Prod. 70 (2007) 1946-1950.[8] P.L. Katavic, D.A. Venables, G.P. Guymer, et al., Alkaloids with human delta-opioid receptor binding affinity from the Australian rainforest tree Peripentadenia mearsii, J. Nat. Prod. 70 (2007) 1946-1950.
9. [9] I.S. Chen, S.J. Wu, I.L. Tsai, et al., Chemical and bioactive constituents from zanthoxylum simulans, J. Nat. Prod. 57 (1994) 1206-1211.[9] I.S. Chen, S.J. Wu, I.L. Tsai, et al., Chemical and bioactive constituents from zanthoxylum simulans, J. Nat. Prod. 57 (1994) 1206-1211.
10. [10] K.D. McBrien, Q. Gao, S. Huang, et al., Fusaricide, a new cytotoxic N-hydroxypyridone from Fusarium sp., J. Nat. Prod. 59 (1996) 1151-1153.[10] K.D. McBrien, Q. Gao, S. Huang, et al., Fusaricide, a new cytotoxic N-hydroxypyridone from Fusarium sp., J. Nat. Prod. 59 (1996) 1151-1153.
11. [11] R.R. Kumar, S. Perumal, P. Senthilkumar, P. Yogeeswari, D. Sriram, An atom efficient, solvent-free, green synthesis and antimycobacterial evaluation of 2-amino-6-methyl-4-aryl-8-[(E)-arylmethylidene]-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridine-3-carbonitriles, Bioorg. Med. Chem. Lett. 17 (2007) 6459-6462.[11] R.R. Kumar, S. Perumal, P. Senthilkumar, P. Yogeeswari, D. Sriram, An atom efficient, solvent-free, green synthesis and antimycobacterial evaluation of 2-amino-6-methyl-4-aryl-8-[(E)-arylmethylidene]-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridine-3-carbonitriles, Bioorg. Med. Chem. Lett. 17 (2007) 6459-6462.
12. [12] M.N. Erichsen, T.H.V. Huynh, B. Abrahamsen, et al., Structure-activity relationship study of first selective inhibitor of excitatory amino acid transporter subtype 1: 2-amino-4-(4-methoxyphenyl)-7-(naphthalen-1-yl)-5-oxo-5, 6,7,8-tetrahydro-4H-chromene-3-carbonitrile (UCPH-101), J. Med. Chem. 53 (2010) 7180-7191.[12] M.N. Erichsen, T.H.V. Huynh, B. Abrahamsen, et al., Structure-activity relationship study of first selective inhibitor of excitatory amino acid transporter subtype 1: 2-amino-4-(4-methoxyphenyl)-7-(naphthalen-1-yl)-5-oxo-5, 6,7,8-tetrahydro-4H-chromene-3-carbonitrile (UCPH-101), J. Med. Chem. 53 (2010) 7180-7191.
13. [13] R. Doostmohammadi, M.T. Maghsoodlou, N. Hazeri, et al., An efficient one-pot multi-component synthesis of 3,4,5-substituted furan-2(5H)-ones catalyzed by tetra-n-butylammonium bisulfate, Chin. Chem. Lett. 24 (2013) 901-903.[13] R. Doostmohammadi, M.T. Maghsoodlou, N. Hazeri, et al., An efficient one-pot multi-component synthesis of 3,4,5-substituted furan-2(5H)-ones catalyzed by tetra-n-butylammonium bisulfate, Chin. Chem. Lett. 24 (2013) 901-903.
14. [14] N. Foroughifar, S. Ebrahimi, One-pot synthesis of 1,3-thiazolidin-4-one using Bi(SCH₂COOH)₃ as catalyst, Chin. Chem. Lett. 24 (2013) 389-391.[14] N. Foroughifar, S. Ebrahimi, One-pot synthesis of 1,3-thiazolidin-4-one using Bi(SCH₂COOH)₃ as catalyst, Chin. Chem. Lett. 24 (2013) 389-391.
15. [15] R. Baharfar, S.M. Baghbanian, Synthesis of novel uracil based 2,5-diaminofurans using multi-component reactions, Chin. Chem. Lett. 23 (2012) 677-680.[15] R. Baharfar, S.M. Baghbanian, Synthesis of novel uracil based 2,5-diaminofurans using multi-component reactions, Chin. Chem. Lett. 23 (2012) 677-680.
16. [16] S.L. Wang, Z.G. Han, S.J. Tu, et al., An efficient method for synthesis of pyrano[3,2-c]pyridine derivatives under microwave irradiation, J. Heterocyclic Chem. 46 (2009) 828-831.[16] S.L. Wang, Z.G. Han, S.J. Tu, et al., An efficient method for synthesis of pyrano[3,2-c]pyridine derivatives under microwave irradiation, J. Heterocyclic Chem. 46 (2009) 828-831.
17. [17] Crystallographic data (excluding structure factors) for compound 4a have been deposited with the Cambridge Crystallographic Data Center.[17] Crystallographic data (excluding structure factors) for compound 4a have been deposited with the Cambridge Crystallographic Data Center.

扫一扫看文章

计量

PDF下载量: 0
文章访问数: 1529
HTML全文浏览量: 47

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Effi cient and mild cyclization procedures for the synthesis of novel 2-amino-4H-pyran derivatives with potential antitumor activity

通讯作者: Hang Song,

English

Effi cient and mild cyclization procedures for the synthesis of novel 2-amino-4H-pyran derivatives with potential antitumor activity

Corresponding author: Hang Song,

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

Effi cient and mild cyclization procedures for the synthesis of novel 2-amino-4H-pyran derivatives with potential antitumor activity

通讯作者: Hang Song,

English

Effi cient and mild cyclization procedures for the synthesis of novel 2-amino-4H-pyran derivatives with potential antitumor activity

Corresponding author: Hang Song,

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

文章相关

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs