SCOPUS 정보 검색 플랫폼

Volumn 22, Issue 23, 2011, Pages 2056-2064

Highly enantioselective synthesis of biologically important 2,5-dihydropyrroles via phosphoric acid-catalyzed three-component reactions and evaluation of their cytotoxicity

(4) Shi, Feng a,c Tao, Zhong Lin b Yu, Jie b Tu, Shu Jiang a,c

a SOOCHOW UNIVERSITY (China)

b UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA (China)

c JIANGSU NORMAL UNIVERSITY (China)

Author keywords

[No Author keywords available]

Indexed keywords

2,5 DIHYDROPYRROLE DERIVATIVE; ACETIC ACID DERIVATIVE; ALDEHYDE DERIVATIVE; ANTINEOPLASTIC AGENT; DIETHYL 4 (2 ETHYLBUTANOYL) 5 (4 NITROPHENYL) 1H PYRROLE 2,2 (5H)DICARBOXYLATE; DIETHYL 4 (CYCLOHEXANECARBONYL) 5 (4 NITROPHENYL) 1H PYRROLE 2,2 (5H)DICARBOXYLATE; DIETHYL 4 ACETYL 5 (2 BROMOPHENYL) 1H PYRROLE 2,2 (5H)DICARBOXYLATE; DIETHYL 4 ACETYL 5 (2 NITROPHENYL) 1H PYRROLE 2,2 (5H)DICARBOXYLATE; DIETHYL 4 ACETYL 5 (3 METHOXYPHENYL) 1H PYRROLE 2,2 (5H)DICARBOXYLATE; DIETHYL 4 ACETYL 5 (3 NITROPHENYL) 1H PYRROLE 2,2 (5H)DICARBOXYLATE; DIETHYL 4 ACETYL 5 (3,4 DICHLOROPHENYL) 1H PYRROLE 2,2 (5H)DICARBOXYLATE; DIETHYL 4 ACETYL 5 (4 BROMOPHENYL) 1H PYRROLE 2,2 (5H)DICARBOXYLATE; DIETHYL 4 ACETYL 5 (4 CYANOPHENYL) 1H PYRROLE 2,2 (5H)DICARBOXYLATE; DIETHYL 4 ACETYL 5 (4 FLUOROPHENYL) 1H PYRROLE 2,2 (5H)DICARBOXYLATE; DIETHYL 4 ACETYL 5 (4 METHOXYPHENYL) 1H PYRROLE 2,2 (5H)DICARBOXYLATE; DIETHYL 4 ACETYL 5 (4 METHOXYSTYRYL) 1H PYRROLE 2,2 (5H)DICARBOXYLATE; DIETHYL 4 ACETYL 5 (4 NITROPHENYL) 1H PYRROLE 2,2 (5H)DICARBOXYLATE; DIETHYL 4 ACETYL 5 (FURAN 2 YL) 1H PYRROLE 2,2 (5H)DICARBOXYLATE; DIETHYL 4 ACETYL 5 (NAPHTHALEN 2 YL) 1H PYRROLE 2,2 (5H)DICARBOXYLATE; DIETHYL 4 ACETYL 5 (THIOPHEN 2 YL) 1H PYRROLE 2,2 (5H)DICARBOXYLATE; DIETHYL 4 ACETYL 5 4 TOLYL 1H PYRROLE 2,2 (5H)DICARBOXYLATE; DIETHYL 4 ACETYL 5 [4 (METHYLSULFONYL)PHENYL] 1H PYRROLE 2,2 (5H)DICARBOXYLATE; DIETHYL 4 ACETYL 5 CYCLOHEXYL 1H PYRROLE 2,2 (5H)DICARBOXYLATE; DIETHYL 4 ACETYL 5 PHENYL 1H PYRROLE 2,2 (5H)DICARBOXYLATE; DIETHYL 5 (4 NITROPHENYL) 4 (2 NITROPHENY) 1H PYRROLE 2,2 (5H)DICARBOXYLATE; DIETHYL 5 (4 NITROPHENYL) 4 (3 PHENYLPROPANOYL) 1H PYRROLE 2,2 (5H)DICARBOXYLATE; DIETHYL 5 (4 NITROPHENYL) 4 NONANOYL 1H PYRROLE 2,2 (5H)DICARBOXYLATE; ESTER; PHOSPHORIC ACID; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CARCINOMA; CARCINOMA CELL; CATALYSIS; CHIRALITY; CYCLOADDITION; CYTOTOXICITY; DRUG DETERMINATION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HUMAN; HUMAN CELL; PRIORITY JOURNAL;

EID: 84862966404 PISSN: 09574166 EISSN: 1362511X Source Type: Journal
DOI: 10.1016/j.tetasy.2011.11.020 Document Type: Article

Times cited : (24)

References (41)

1
- 84889434690
- Wiley-VCH Verlag GmbH & Co. KGaA Weinheim
- E. Fattorusso, and O. Taglialatela-Scafati Modern Alkaloids: Structure, Isolation, Synthesis and Biology 2008 Wiley-VCH Verlag GmbH & Co. KGaA Weinheim
- (2008) Modern Alkaloids: Structure, Isolation, Synthesis and Biology
- Fattorusso, E.¹ Taglialatela-Scafati, O.²

2
- 0025972133
- S. Carmeli, R.E. Moore, and G.M.L. Patterson Tetrahedron 47 1991 2087
- (1991) Tetrahedron , vol.47 , pp. 2087
- Carmeli, S.¹ Moore, R.E.² Patterson, G.M.L.³

3
- 0023580041
- W.K. Anderson, and A.S. Milowsky J. Med. Chem. 30 1987 2144
- (1987) J. Med. Chem. , vol.30 , pp. 2144
- Anderson, W.K.¹ Milowsky, A.S.²

4
- 17744417463
- A. Fürstner Angew. Chem., Int. Ed. 42 2003 3582
- (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 3582
- Fürstner, A.¹

5
- 75749099813
- T. Ritthiwigrom, A.C. Willis, and S.G. Pyne J. Org. Chem. 75 2010 815
- (2010) J. Org. Chem. , vol.75 , pp. 815
- Ritthiwigrom, T.¹ Willis, A.C.² Pyne, S.G.³

6
- 0036255422
- K.B. Lindsay, M. Tang, and S.G. Pyne Synlett 2002 731
- (2002) Synlett , pp. 731
- Lindsay, K.B.¹ Tang, M.² Pyne, S.G.³

7
- 0029869765
- C. Cinquin, M. Bortolussi, and R. Bloch Tetrahedron 52 1996 6943
- (1996) Tetrahedron , vol.52 , pp. 6943
- Cinquin, C.¹ Bortolussi, M.² Bloch, R.³

8
- 79959658123
- For related asymmetric syntheses of pyrrole derivatives, see
- For related asymmetric syntheses of pyrrole derivatives, see: J. Song, C. Guo, P.-H. Chen, J. Yu, S.-W. Luo, and L.-Z. Gong Chem. Eur. J. 17 2011 7786
- (2011) Chem. Eur. J. , vol.17 , pp. 7786
- Song, J.¹ Guo, C.² Chen, P.-H.³ Yu, J.⁴ Luo, S.-W.⁵ Gong, L.-Z.⁶

9
- 80054705902
- S. Guo, Y. Xie, X. Hu, and H. Huang Org. Lett. 13 2011 5596
- (2011) Org. Lett. , vol.13 , pp. 5596
- Guo, S.¹ Xie, Y.² Hu, X.³ Huang, H.⁴

10
- 48249149097
- W.-Q. Wu, Q. Peng, D.-X. Dong, X.-L. Hou, and Y.-D. Wu J. Am. Chem. Soc. 130 2008 9717
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 9717
- Wu, W.-Q.¹ Peng, Q.² Dong, D.-X.³ Hou, X.-L.⁴ Wu, Y.-D.⁵

11
- 38349135761
- R. Kuwano, M. Kashiwabara, M. Ohsumi, and H. Kusano J. Am. Chem. Soc. 130 2008 808
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 808
- Kuwano, R.¹ Kashiwabara, M.² Ohsumi, M.³ Kusano, H.⁴

12
- 0032572831
- M.C. Krishna, W. DeGraff, O.H. Hankovszky, C.P. Sar, T. Kalai, J. Jeko, A. Russo, J.B. Mitchell, and K. Hideg J. Med. Chem. 41 1998 3477
- (1998) J. Med. Chem. , vol.41 , pp. 3477
- Krishna, M.C.¹ Degraff, W.² Hankovszky, O.H.³ Sar, C.P.⁴ Kalai, T.⁵ Jeko, J.⁶ Russo, A.⁷ Mitchell, J.B.⁸ Hideg, K.⁹

13
- 0037120829
- Y. Lee, K.-Q. Ling, X. Lu, R.B. Silverman, E.M. Shepard, D.M. Dooley, and L.M. Sayre J. Am. Chem. Soc. 124 2002 12135
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 12135
- Lee, Y.¹ Ling, K.-Q.² Lu, X.³ Silverman, R.B.⁴ Shepard, E.M.⁵ Dooley, D.M.⁶ Sayre, L.M.⁷

14
- 0002683459
- V.L. Gein, E.V. Voronina, T.E. Ryumina, G.N. Novoselova, K.D. Potemkin, and Y.S. Andreichikov Khim.-Farmatsevticheskii Zh. 30 1996 25
- (1996) Khim.-Farmatsevticheskii Zh. , vol.30 , pp. 25
- Gein, V.L.¹ Voronina, E.V.² Ryumina, T.E.³ Novoselova, G.N.⁴ Potemkin, K.D.⁵ Andreichikov, Y.S.⁶

15
- 0018386004
- J.K. Sugden, and M.R. Tavakoli Saberi Eur. J. Med. Chem. 14 1979 189
- (1979) Eur. J. Med. Chem. , vol.14 , pp. 189
- Sugden, J.K.¹ Tavakoli Saberi, M.R.²

16
- 84862914749
- U.S. Pat. Appl. Publ. US 20110136752 A1 20110609
- Peoples, A.; Ling, L. L.; Lewis, K.; Zhang, Z. U.S. Pat. Appl. Publ. 2011, US 20110136752 A1 20110609.
- (2011)
- Peoples, A.¹ Ling, L.L.² Lewis, K.³ Zhang, Z.⁴

17
- 38349189109
- For reviews on chiral Brønsted acid-catalyzed transformations, see
- For reviews on chiral Brønsted acid-catalyzed transformations, see: T. Akiyama Chem. Rev. 107 2007 5744
- (2007) Chem. Rev. , vol.107 , pp. 5744
- Akiyama, T.¹

18
- 38349135345
- A.G. Doyle, and E.N. Jacobsen Chem. Rev. 107 2007 5713
- (2007) Chem. Rev. , vol.107 , pp. 5713
- Doyle, A.G.¹ Jacobsen, E.N.²

19
- 52049088477
- M. Terada Chem. Commun. 2008 4097
- (2008) Chem. Commun. , pp. 4097
- Terada, M.¹

20
- 77953261329
- M. Terada Synthesis 2010 1929
- (2010) Synthesis , pp. 1929
- Terada, M.¹

21
- 1942494211
- For accounts of phosphoric acid catalyzed MCRs, see in press. doi: 10.1021/ar2000343
- For accounts of phosphoric acid catalyzed MCRs, see: Yu, J.; Shi, F.; Gong, L.-Z. Acc. Chem. Res., in press. doi: 10.1021/ar2000343.
- Acc. Chem. Res.
- Yu, J.¹ Shi, F.² Gong, L.-Z.³

22
- 80052211267
- F. Shi, S.-W. Luo, Z.-L. Tao, L. He, J. Yu, S.-J. Tu, and L.-Z. Gong Org. Lett. 13 2011 4680
- (2011) Org. Lett. , vol.13 , pp. 4680
- Shi, F.¹ Luo, S.-W.² Tao, Z.-L.³ He, L.⁴ Yu, J.⁵ Tu, S.-J.⁶ Gong, L.-Z.⁷

23
- 69049086649
- B. Jiang, S.-J. Tu, P. Kaur, W. Wever, and G. Li J. Am. Chem. Soc. 131 2009 11660
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 11660
- Jiang, B.¹ Tu, S.-J.² Kaur, P.³ Wever, W.⁴ Li, G.⁵

24
- 77951848693
- B. Jiang, C. Li, F. Shi, S.-J. Tu, P. Kaur, W. Wever, and G. Li J. Org. Chem. 75 2010 2962
- (2010) J. Org. Chem. , vol.75 , pp. 2962
- Jiang, B.¹ Li, C.² Shi, F.³ Tu, S.-J.⁴ Kaur, P.⁵ Wever, W.⁶ Li, G.⁷

25
- 58549102691
- P. Wei, X. Zhang, S. Tu, S. Yan, H. Ying, and P. Ouyang Bioorg. Med. Chem. Lett. 19 2009 828
- (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 828
- Wei, P.¹ Zhang, X.² Tu, S.³ Yan, S.⁴ Ying, H.⁵ Ouyang, P.⁶

26
- 79951669907
- F. Shi, A.-X. Dai, S. Zhang, X.-H. Zhang, and S.-J. Tu Eur. J. Med. Chem. 46 2011 953
- (2011) Eur. J. Med. Chem. , vol.46 , pp. 953
- Shi, F.¹ Dai, A.-X.² Zhang, S.³ Zhang, X.-H.⁴ Tu, S.-J.⁵

27
- 79951720545
- F. Shi, J. Ding, S. Zhang, W.-J. Hao, C. Cheng, and S. Tu Bioorg. Med. Chem. Lett. 21 2011 1554
- (2011) Bioorg. Med. Chem. Lett. , vol.21 , pp. 1554
- Shi, F.¹ Ding, J.² Zhang, S.³ Hao, W.-J.⁴ Cheng, C.⁵ Tu, S.⁶

28
- 61349181405
- W.-J. Liu, X.-H. Chen, and L.-Z. Gong Org. Lett. 10 2008 5357
- (2008) Org. Lett. , vol.10 , pp. 5357
- Liu, W.-J.¹ Chen, X.-H.² Gong, L.-Z.³

29
- 75949128866
- S. Grguric-Sipka, I. Ivanovic, G. Rakic, N. Todorovic, N. Gligorijevic, S. Radulovic, V.B. Arion, B.K. Keppler, and Z.L. Tesic Eur. J. Med. Chem. 45 2010 1051
- (2010) Eur. J. Med. Chem. , vol.45 , pp. 1051
- Grguric-Sipka, S.¹ Ivanovic, I.² Rakic, G.³ Todorovic, N.⁴ Gligorijevic, N.⁵ Radulovic, S.⁶ Arion, V.B.⁷ Keppler, B.K.⁸ Tesic, Z.L.⁹

30
- 76149093845
- T. de Haro, and C. Nevado J. Am. Chem. Soc. 132 2010 1512
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 1512
- De Haro, T.¹ Nevado, C.²

31
- 2342521907
- D. Uraguchi, and M. Tereda J. Am. Chem. Soc. 126 2004 5356
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 5356
- Uraguchi, D.¹ Tereda, M.²

32
- 24044538628
- T. Akiyam, H. Morita, J. Itoh, and K. Fuchibe Org. Lett. 7 2005 2583
- (2005) Org. Lett. , vol.7 , pp. 2583
- Akiyam, T.¹ Morita, H.² Itoh, J.³ Fuchibe, K.⁴

33
- 30744477746
- R.I. Storer, D.E. Carrera, Y. Ni, and D.W.C. Macmillan J. Am. Chem. Soc. 128 2006 84
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 84
- Storer, R.I.¹ Carrera, D.E.² Ni, Y.³ MacMillan, D.W.C.⁴

34
- 33746292951
- D. Uraguchi, K. Sorimachi, and M. Terada Angew. Chem., Int. Ed. 45 2006 2254
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 2254
- Uraguchi, D.¹ Sorimachi, K.² Terada, M.³

35
- 84962407641
- M. Yamanaka, Junji Itoh, K. Fuchibe, and T. Akiyama J. Am. Chem. Soc. 129 2007 6756
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 6756
- Yamanaka, M.¹ Itoh, J.² Fuchibe, K.³ Akiyama, T.⁴

36
- 34247112829
- Q.-X. Guo, H. Liu, C. Guo, S.-W. Luo, Y. Gu, and L.-Z. Gong J. Am. Chem. Soc. 129 2007 3790
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 3790
- Guo, Q.-X.¹ Liu, H.² Guo, C.³ Luo, S.-W.⁴ Gu, Y.⁵ Gong, L.-Z.⁶

37
- 42449110313
- J. Jiang, J. Yu, X.-X. Sun, Q.-Q. Rao, and L.-Z. Gong Angew. Chem., Int. Ed. 47 2008 2458
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 2458
- Jiang, J.¹ Yu, J.² Sun, X.-X.³ Rao, Q.-Q.⁴ Gong, L.-Z.⁵

38
- 42649137921
- X.-H. Chen, W.-Q. Zhang, and L.-Z. Gong J. Am. Chem. Soc. 130 2008 5652
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 5652
- Chen, X.-H.¹ Zhang, W.-Q.² Gong, L.-Z.³

39
- 33746801098
- K. Itoh, K. Fuchibe, and T. Akiyama Angew. Chem., Int. Ed. 45 2006 4796
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 4796
- Itoh, K.¹ Fuchibe, K.² Akiyama, T.³

40
- 70350676939
- J. Yu, L. He, X.-H. Chen, J. Song, W.-J. Chen, and L.-Z. Gong Org. Lett. 11 2009 4946
- (2009) Org. Lett. , vol.11 , pp. 4946
- Yu, J.¹ He, L.² Chen, X.-H.³ Song, J.⁴ Chen, W.-J.⁵ Gong, L.-Z.⁶

41
- 80052097397
- L. He, X.-H. Chen, D.-N. Wang, S.-W. Luo, W.-Q. Zhang, J. Yu, L. Ren, and L.-Z. Gong J. Am. Chem. Soc. 133 2011 13504
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 13504
- He, L.¹ Chen, X.-H.² Wang, D.-N.³ Luo, S.-W.⁴ Zhang, W.-Q.⁵ Yu, J.⁶ Ren, L.⁷ Gong, L.-Z.⁸

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.