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

Dao-Cai Wang ^a ,
Yong-Mei Xie ^b ,
Chen Fan ^b ,
Shun Yao ^a ,
Hang Song ^a,,

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
Available Online: 16 April 2014
Fund Project:

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).
- Synthesis,
- 2-Amino-4H-pyran derivatives,
- Multicomponent,
- Anticancer
1. [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.
2. [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.
3. [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.
4. [4]
  [4] I.S. Chen, I.W. Tsai, C.M. Teng, et al., Pyranoquinoline alkaloids from Zanthoxylum simulans, Phytochemistry 46 (1997) 525-529.
5. [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.
6. [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.
7. [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.
8. [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.
9. [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.
10. [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.
11. [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.
12. [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.
13. [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.
14. [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.
15. [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.
16. [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.
17. [17]
  [17] Crystallographic data (excluding structure factors) for compound 4a have been deposited with the Cambridge Crystallographic Data Center.
1. [1]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
5. [5]
  Yi Luo , Lin Dong . Multicomponent remote C(sp²)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
6. [6]
  Shangqian Zhang , Jiaxuan Li , Xuan Hu , Zelong Chen , Junliang Dong , Chenhao Hu , Shuang Chao , Yinghua Lv , Yuxin Pei , Zhichao Pei . H₂S and NIR light-driven nanomotors induce disulfidptosis for targeted anticancer therapy by enhancing disruption of tumor metabolic symbiosis. Chinese Chemical Letters, 2025, 36(1): 110314-. doi: 10.1016/j.cclet.2024.110314
7. [7]
  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
8. [8]
  Wei-Tao Dou , Qing-Wen Zeng , Yan Kang , Haidong Jia , Yulian Niu , Jinglong Wang , Lin Xu . Construction and application of multicomponent fluorescent droplets. Chinese Chemical Letters, 2025, 36(1): 109995-. doi: 10.1016/j.cclet.2024.109995
9. [9]
  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
10. [10]
  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
11. [11]
  Wenkai Liu , Yanxian Hou , Weijian Liu , Ran Wang , Shan He , Xiang Xia , Chengyuan Lv , Hua Gu , Qichao Yao , Qingze Pan , Zehou Su , Danhong Zhou , Wen Sun , Jiangli Fan , Xiaojun Peng . Se-substituted pentamethine cyanine for anticancer photodynamic therapy mediated using the hot band absorption process. Chinese Chemical Letters, 2024, 35(12): 109631-. doi: 10.1016/j.cclet.2024.109631
12. [12]
  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
13. [13]
  Liyong Ding , Zhenhua Pan , Qian Wang . 2D photocatalysts for hydrogen peroxide synthesis. Chinese Chemical Letters, 2024, 35(12): 110125-. doi: 10.1016/j.cclet.2024.110125
14. [14]
  Tong Tong , Lezong Chen , Siying Wu , Zhong Cao , Yuanbin Song , Jun Wu . Establishment of a leucine-based poly(ester amide)s library with self-anticancer effect as nano-drug carrier for colorectal cancer treatment. Chinese Chemical Letters, 2024, 35(12): 109689-. doi: 10.1016/j.cclet.2024.109689
15. [15]
  Ying Li , Long-Jie Wang , Yong-Kang Zhou , Jun Liang , Bin Xiao , Ji-Shen Zheng . An improved installation of 2-hydroxy-4-methoxybenzyl (iHmb) method for chemical protein synthesis. Chinese Chemical Letters, 2024, 35(5): 109033-. doi: 10.1016/j.cclet.2023.109033
16. [16]
  Zhixiang Li , Zhirong Yang , Chang Yao , Bin Wu , Gang Qian , Xuezhi Duan , Xinggui Zhou , Jing Zhang . Efficient continuous synthesis of 2-hydroxycarbazole and 4-hydroxycarbazole in a millimeter scale photoreactor. Chinese Chemical Letters, 2024, 35(4): 108893-. doi: 10.1016/j.cclet.2023.108893
17. [17]
  Juanjuan Wang , Fang Wang , Bin Qin , Yue Wu , Huan Yang , Xiaolong Li , Lanfang Wang , Xiufang Qin , Xiaohong Xu . Controlled synthesis and excellent magnetism of ferrimagnetic NiFe₂Se₄ nanostructures. Chinese Chemical Letters, 2024, 35(11): 109449-. doi: 10.1016/j.cclet.2023.109449
18. [18]
  Shuwen SUN , Gaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399
19. [19]
  Xiang Huang , Dongzhen Xu , Yang Liu , Xia Huang , Yangfan Wu , Dongmei Fang , Bing Xia , Wei Jiao , Jian Liao , Min Wang . Asymmetric synthesis of difluorinated α-quaternary amino acids (DFAAs) via Cu-catalyzed difluorobenzylation of aldimine esters. Chinese Chemical Letters, 2024, 35(12): 109665-. doi: 10.1016/j.cclet.2024.109665
20. [20]
  Min-Hang Zhou , Jun Jiang , Wei-Min He . EDA-complexes-enabled photochemical synthesis of α-amino acids with imines and tetrabutylammonium oxalate. Chinese Chemical Letters, 2025, 36(1): 110446-. doi: 10.1016/j.cclet.2024.110446

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(608)
HTML views(17)

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