SCOPUS 정보 검색 플랫폼

Organic and Biomolecular Chemistry

Volumn 11, Issue 25, 2013, Pages 4154-4163

Synthesis and biological evaluation of new paclitaxel analogs and discovery of potent antitumor agents

(2) Nicolaou, Kyriacos C a,b,c Valiulin, Roman A a

a SCRIPPS RESEARCH INSTITUTE (United States)

b UNIVERSITY OF CALIFORNIA (United States)

c RICE UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

10-DEACETYLBACCATIN III; ANTI-TUMOR AGENTS; ANTICANCER ACTIVITIES; BIOLOGICAL EVALUATION; NATIONAL CANCER INSTITUTE; RELATED COMPOUNDS; SCREENING PROGRAMS; SODIUM BORO HYDRIDES;

CELL CULTURE; SOFTWARE TESTING; SYNTHESIS (CHEMICAL);

DRUG PRODUCTS;

10 DEACETYLBACCATINE III; 10-DEACETYLBACCATINE III; ANTINEOPLASTIC AGENT; DOCETAXEL; DRUG DERIVATIVE; PACLITAXEL; TAXOID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG SCREENING; HALOGENATION; HUMAN; NEOPLASM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TAXUS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HALOGENATION; HUMANS; MODELS, MOLECULAR; NEOPLASMS; PACLITAXEL; STRUCTURE-ACTIVITY RELATIONSHIP; TAXOIDS; TAXUS;

EID: 84878799625 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c3ob40654g Document Type: Article

Times cited : (22)

References (58)

1
- 84864367909
- F. Bray A. Jemal N. Grey J. Ferlay D. Forman Lancet Oncol. 2012 13 790 801
- (2012) Lancet Oncol. , vol.13 , pp. 790-801
- Bray, F.¹ Jemal, A.² Grey, N.³ Ferlay, J.⁴ Forman, D.⁵

2
- 33748226949
- K. C. Nicolaou W.-M. Dai R. K. Guy Angew. Chem., Int. Ed. Engl. 1994 33 15 44
- (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 15-44
- Nicolaou, K.C.¹ Dai, W.-M.² Guy, R.K.³

3
- 84878779025
- U.s. Department Of Health And Human Services National Library of Medicine, 193-220
- U.S. Department of Health and Human Services, Medical Subject Headings, Tree Structures, 2003, National Library of Medicine, 2002, pp. 193-220
- (2002) Medical Subject Headings, Tree Structures, 2003

4
- 0003998061
- in, Lippincott Williams & Wilkins, 7th edn, 1-1488, 2, 1489-2898
- V. T. DeVita Jr, S. Hellman and S. A. Rosenberg, in Cancer: Principles and Practice of Oncology, Lippincott Williams & Wilkins, 7th edn, 2005, vol. 1, pp. 1-1488, vol. 2, pp. 1489-2898
- (2005) Cancer: Principles and Practice of Oncology , vol.1
- Devita Jr., V.T.¹ Hellman, S.² Rosenberg, S.A.³

5
- 0003964363
- American Cancer Society, Atlanta, 1-64
- Cancer Facts & Figures 2012, American Cancer Society, Atlanta, 2012, pp. 1-64
- (2012) Cancer Facts & Figures 2012

6
- 84892673187
- http://disease-ontology.org/

7
- 48249096043
- in, Wiley-VCH, Weinheim, 1-366
- K. C. Nicolaou and T. Montagnon, in Molecules that Changed the World, Wiley-VCH, Weinheim, 2008, pp. 1-366
- (2008) Molecules That Changed the World
- Nicolaou, K.C.¹ Montagnon, T.²

8
- 62149144449
- K. C. Nicolaou J. S. Chen S. M. Dalby Bioorg. Med. Chem. 2009 17 2290 2303
- (2009) Bioorg. Med. Chem. , vol.17 , pp. 2290-2303
- Nicolaou, K.C.¹ Chen, J.S.² Dalby, S.M.³

9
- 0015211527
- M. C. Wani H. L. Taylor M. E. Wall P. Coggon A. T. McPhail J. Am. Chem. Soc. 1971 93 2325 2327
- (1971) J. Am. Chem. Soc. , vol.93 , pp. 2325-2327
- Wani, M.C.¹ Taylor, H.L.² Wall, M.E.³ Coggon, P.⁴ McPhail, A.T.⁵

10
- 80155147586
- Y.-F. Wang Q.-W. Shi M. Dong H. Kiyota Y.-C. Gu B. Cong Chem. Rev. 2011 111 7652 7709
- (2011) Chem. Rev. , vol.111 , pp. 7652-7709
- Wang, Y.-F.¹ Shi, Q.-W.² Dong, M.³ Kiyota, H.⁴ Gu, Y.-C.⁵ Cong, B.⁶

11
- 0018387446
- P. B. Schiff J. Fant S. B. Horwitz Nature 1979 277 665 667
- (1979) Nature , vol.277 , pp. 665-667
- Schiff, P.B.¹ Fant, J.² Horwitz, S.B.³

12
- 84892668774
- http://www.cancer.gov/cancertopics/druginfo/paclitaxel

13
- 84892676128
- http://www.cancer.gov/cancertopics/druginfo/docetaxel

14
- 28144445570
- K. A. Lyseng-Williamson C. Fenton Drugs 2005 65 2513 2531
- (2005) Drugs , vol.65 , pp. 2513-2531
- Lyseng-Williamson, K.A.¹ Fenton, C.²

15
- 79151470222
- P. A. Arroyo R. U. Pérez B. C. Díez M. A. F. Feijóo J. H. Magdalena M. A. C. Hernández Cancer Treat. Rev. 2011 37 105 110
- (2011) Cancer Treat. Rev. , vol.37 , pp. 105-110
- Arroyo, P.A.¹ Pérez, R.U.² Díez, B.C.³ Feijóo, M.A.F.⁴ Magdalena, J.H.⁵ Hernández, M.A.C.⁶

16
- 0027252973
- G. Samaranayake K. A. Neidigh D. G. I. Kingston J. Nat. Prod. 1993 56 884 898
- (1993) J. Nat. Prod. , vol.56 , pp. 884-898
- Samaranayake, G.¹ Neidigh, K.A.² Kingston, D.G.I.³

17
- 0027935479
- I. Ojima O. Duclos M. Zucco M.-C. Bissery C. Combeau P. Vrignaud J. F. Riou F. Lavelle J. Med. Chem. 1994 37 2602 2608
- (1994) J. Med. Chem. , vol.37 , pp. 2602-2608
- Ojima, I.¹ Duclos, O.² Zucco, M.³ Bissery, M.-C.⁴ Combeau, C.⁵ Vrignaud, P.⁶ Riou, J.F.⁷ Lavelle, F.⁸

18
- 0032548461
- I. Ojima P.-Y. Bounaud C. Takeuchi P. Pera R. J. Bernacki Bioorg. Med. Chem. Lett. 1998 8 189 194
- (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 189-194
- Ojima, I.¹ Bounaud, P.-Y.² Takeuchi, C.³ Pera, P.⁴ Bernacki, R.J.⁵

19
- 0034728938
- J. Dubois S. Thoret F. Guéritte D. Guénard Tetrahedron Lett. 2000 41 3331 3334
- (2000) Tetrahedron Lett. , vol.41 , pp. 3331-3334
- Dubois, J.¹ Thoret, S.² Guéritte, F.³ Guénard, D.⁴

20
- 0034677975
- Q. Cheng T. Oritani T. Horiguchi Tetrahedron 2000 56 1667 1679
- (2000) Tetrahedron , vol.56 , pp. 1667-1679
- Cheng, Q.¹ Oritani, T.² Horiguchi, T.³

21
- 0035847675
- S. Iimura K. Uoto S. Ohsuki J. Chiba T. Yoshino M. Iwahana T. Jimbo H. Terasawa T. Soga Bioorg. Med. Chem. Lett. 2001 11 407 410
- (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 407-410
- Iimura, S.¹ Uoto, K.² Ohsuki, S.³ Chiba, J.⁴ Yoshino, T.⁵ Iwahana, M.⁶ Jimbo, T.⁷ Terasawa, H.⁸ Soga, T.⁹

22
- 16044369708
- J. Kant W. S. Schwartz C. Fairchild Q. Gao S. Huang B. H. Long J. F. Kadow D. R. Langley V. Farina D. Vyas Tetrahedron Lett. 1996 37 6495 6498
- (1996) Tetrahedron Lett. , vol.37 , pp. 6495-6498
- Kant, J.¹ Schwartz, W.S.² Fairchild, C.³ Gao, Q.⁴ Huang, S.⁵ Long, B.H.⁶ Kadow, J.F.⁷ Langley, D.R.⁸ Farina, V.⁹ Vyas, D.¹⁰

23
- 0031049783
- I. Ojima S. D. Kuduk P. Pera J. M. Veith R. J. Bernacki J. Med. Chem. 1997 40 279 285
- (1997) J. Med. Chem. , vol.40 , pp. 279-285
- Ojima, I.¹ Kuduk, S.D.² Pera, P.³ Veith, J.M.⁴ Bernacki, R.J.⁵

24
- 0043234178
- O. Querolle J. Dubois S. Thoret F. Roussi S. Montiel-Smith F. Guéritte D. Guénard J. Med. Chem. 2003 46 3623 3630
- (2003) J. Med. Chem. , vol.46 , pp. 3623-3630
- Querolle, O.¹ Dubois, J.² Thoret, S.³ Roussi, F.⁴ Montiel-Smith, S.⁵ Guéritte, F.⁶ Guénard, D.⁷

25
- 0037533959
- I. Ojima C. L. Fumero-Oderda S. D. Kuduk Z. Ma F. Kirikae T. Kirikae Bioorg. Med. Chem. 2003 11 2867 2888
- (2003) Bioorg. Med. Chem. , vol.11 , pp. 2867-2888
- Ojima, I.¹ Fumero-Oderda, C.L.² Kuduk, S.D.³ Ma, Z.⁴ Kirikae, F.⁵ Kirikae, T.⁶

26
- 8644245900
- O. Querolle J. Dubois S. Thoret F. Roussi F. Guéritte D. Guénard J. Med. Chem. 2004 47 5937 5944
- (2004) J. Med. Chem. , vol.47 , pp. 5937-5944
- Querolle, O.¹ Dubois, J.² Thoret, S.³ Roussi, F.⁴ Guéritte, F.⁵ Guénard, D.⁶

27
- 50049108113
- B. Ke Y. Qin F. Zhao Y. Qu Bioorg. Med. Chem. Lett. 2008 18 4783 4785
- (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 4783-4785
- Ke, B.¹ Qin, Y.² Zhao, F.³ Qu, Y.⁴

28
- 79953210706
- H.-F. Lu C. Xie J. Chang G.-Q. Lin X. Sun Eur. J. Med. Chem. 2011 46 1743 1748
- (2011) Eur. J. Med. Chem. , vol.46 , pp. 1743-1748
- Lu, H.-F.¹ Xie, C.² Chang, J.³ Lin, G.-Q.⁴ Sun, X.⁵

29
- 0025871603
- G. Samaranayake N. F. Magri C. Jitrangsri D. G. I. Kingston J. Org. Chem. 1991 56 5114 5119
- (1991) J. Org. Chem. , vol.56 , pp. 5114-5119
- Samaranayake, G.¹ Magri, N.F.² Jitrangsri, C.³ Kingston, D.G.I.⁴

30
- 0026781180
- A. Wahl F. Guéritte-Voegelein D. Guénard M.-T. Le Goff P. Potier Tetrahedron 1992 48 6965 6974
- (1992) Tetrahedron , vol.48 , pp. 6965-6974
- Wahl, A.¹ Guéritte-Voegelein, F.² Guénard, D.³ Le Goff, M.-T.⁴ Potier, P.⁵

31
- 0027418091
- S.-H. Chen S. Huang J. Wei V. Farina Tetrahedron 1993 49 2805 2828
- (1993) Tetrahedron , vol.49 , pp. 2805-2828
- Chen, S.-H.¹ Huang, S.² Wei, J.³ Farina, V.⁴

32
- 0028032635
- J.-P. Pulicani B. Hervé J.-D. Bourzat A. Commerçon Tetrahedron Lett. 1994 35 9709 9712
- (1994) Tetrahedron Lett. , vol.35 , pp. 9709-9712
- Pulicani, J.-P.¹ Hervé, B.² Bourzat, J.-D.³ Commerçon, A.⁴

33
- 0027994560
- S.-H. Chen V. Farina S. Huang Q. Gao J. Golik T. W. Doyle Tetrahedron 1994 50 8633 8650
- (1994) Tetrahedron , vol.50 , pp. 8633-8650
- Chen, S.-H.¹ Farina, V.² Huang, S.³ Gao, Q.⁴ Golik, J.⁵ Doyle, T.W.⁶

34
- 0028296779
- S.-H. Chen S. Huang Q. Gao J. Golik V. Farina J. Org. Chem. 1994 59 1475 1484
- (1994) J. Org. Chem. , vol.59 , pp. 1475-1484
- Chen, S.-H.¹ Huang, S.² Gao, Q.³ Golik, J.⁴ Farina, V.⁵

35
- 0030910079
- C. Yu Z. Liu Tetrahedron Lett. 1997 38 4133 4136
- (1997) Tetrahedron Lett. , vol.38 , pp. 4133-4136
- Yu, C.¹ Liu, Z.²

36
- 15144348920
- R. A. Johnson P. J. Dobrowolski E. G. Nidy I. Gebhard S. J. Qualls N. A. Wicnienski R. C. Kelly T. W. Pitts N. M. Lopes T. F. DeKoning S. J. Mattern S. D. Weed J. P. McGovren C. G. Chidester J. Med. Chem. 1997 40 2810 2812
- (1997) J. Med. Chem. , vol.40 , pp. 2810-2812
- Johnson, R.A.¹ Dobrowolski, P.J.² Nidy, E.G.³ Gebhard, I.⁴ Qualls, S.J.⁵ Wicnienski, N.A.⁶ Kelly, R.C.⁷ Pitts, T.W.⁸ Lopes, N.M.⁹ Dekoning, T.F.¹⁰ Mattern, S.J.¹¹ Weed, S.D.¹² McGovren, J.P.¹³ Chidester, C.G.¹⁴

37
- 78649828718
- Y. Zhao H.-B. Zhang J.-K. Liu J. Su Y. Li Z.-J. Yao Q.-S. Zhao Tetrahedron Lett. 2011 52 139 142
- (2011) Tetrahedron Lett. , vol.52 , pp. 139-142
- Zhao, Y.¹ Zhang, H.-B.² Liu, J.-K.³ Su, J.⁴ Li, Y.⁵ Yao, Z.-J.⁶ Zhao, Q.-S.⁷

38
- 83455201065
- F. Gao Z.-K. Yang Q.-H. Chen X.-G. Chen F.-P. Wang Org. Biomol. Chem. 2012 10 361 366
- (2012) Org. Biomol. Chem. , vol.10 , pp. 361-366
- Gao, F.¹ Yang, Z.-K.² Chen, Q.-H.³ Chen, X.-G.⁴ Wang, F.-P.⁵

39
- 0001365893
- J. Fried E. F. Sabo J. Am. Chem. Soc. 1954 76 1455 1456
- (1954) J. Am. Chem. Soc. , vol.76 , pp. 1455-1456
- Fried, J.¹ Sabo, E.F.²

40
- 0029010769
- P. A. Bartlett A. Otake J. Org. Chem. 1995 60 3107 3111
- (1995) J. Org. Chem. , vol.60 , pp. 3107-3111
- Bartlett, P.A.¹ Otake, A.²

41
- 33645454126
- C. Isanbor D. O'Hagan J. Fluorine Chem. 2006 127 303 319
- (2006) J. Fluorine Chem. , vol.127 , pp. 303-319
- Isanbor, C.¹ O'Hagan, D.²

42
- 33746372978
- K. L. Kirk J. Fluorine Chem. 2006 127 1013 1029
- (2006) J. Fluorine Chem. , vol.127 , pp. 1013-1029
- Kirk, K.L.¹

43
- 77958039726
- D. O'Hagan J. Fluorine Chem. 2010 131 1071 1081
- (2010) J. Fluorine Chem. , vol.131 , pp. 1071-1081
- O'Hagan, D.¹

44
- 83455243028
- L. E. Zimmer C. Sparr R. Gilmour Angew. Chem., Int. Ed. 2011 50 11860 11871
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 11860-11871
- Zimmer, L.E.¹ Sparr, C.² Gilmour, R.³

45
- 84892674308
- http://dtp.nci.nih.gov/

46
- 0003579939
- in, John Wiley & Sons, 2nd edn, 1-12094 (14 volumes) Albeit this particular conversion was previously unknown, Kant et al. from Bristol-Myers Squibb Research Institute observed similar undesired side-product while preparing C-10 Taxol® analogs
- L. A. Paquette, D. Crich, P. L. Fuchs and G. Molander, in Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, 2nd edn, 2009, pp. 1-12094 (14 volumes)
- (2009) Encyclopedia of Reagents for Organic Synthesis
- Paquette, L.A.¹ Crich, D.² Fuchs, P.L.³ Molander, G.⁴

47
- 0027981391
- J. Kant W. S. O'Keeffe S.-H. Chen V. Farina C. Fairchild K. Johnston J. F. Kadow B. H. Long D. Vyas Tetrahedron Lett. 1994 35 5543 5546
- (1994) Tetrahedron Lett. , vol.35 , pp. 5543-5546
- Kant, J.¹ O'Keeffe, W.S.² Chen, S.-H.³ Farina, V.⁴ Fairchild, C.⁵ Johnston, K.⁶ Kadow, J.F.⁷ Long, B.H.⁸ Vyas, D.⁹

48
- 0023678710
- Intermediate 5d, under warmer temperature and prolonged treatment, is prone to rearrangement, producing taxyunansin-related 37 motif 6 through A-ring contraction, as previously reported by Kingston, 29 Liu, 35 and Chen. 50,51 In the presence of moisture 5d hydrolyzes, forming a mixture of two diastereomeric sulfinamides (7 or 7′, which were observed exclusively in the reaction between 13-acetylbaccatin III and DAST): 51
- J.-N. Denis A. E. Greene J. Am. Chem. Soc. 1988 110 5917 5919
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 5917-5919
- Denis, J.-N.¹ Greene, A.E.²

49
- 0027452469
- S.-H. Chen S. Huang J. Wei V. Farina J. Org. Chem. 1993 58 4520 4521
- (1993) J. Org. Chem. , vol.58 , pp. 4520-4521
- Chen, S.-H.¹ Huang, S.² Wei, J.³ Farina, V.⁴

50
- 0028147398
- S.-H. Chen S. Huang V. Farina Tetrahedron Lett. 1994 35 41 44
- (1994) Tetrahedron Lett. , vol.35 , pp. 41-44
- Chen, S.-H.¹ Huang, S.² Farina, V.³

51
- 0028939437
- No cyclopropane-containing compound was isolated in the reaction, see
- G. P. Roth D. R. Marshall S.-H. Chen Tetrahedron Lett. 1995 36 1609 1612
- (1995) Tetrahedron Lett. , vol.36 , pp. 1609-1612
- Roth, G.P.¹ Marshall, D.R.² Chen, S.-H.³

52
- 0027997056
- see also ref. 49-51
- R. A. Johnson E. G. Nidy P. J. Dobrowolski I. Gebhard S. J. Qualls N. A. Wicnienski R. C. Kelly Tetrahedron Lett. 1994 35 7893 7896
- (1994) Tetrahedron Lett. , vol.35 , pp. 7893-7896
- Johnson, R.A.¹ Nidy, E.G.² Dobrowolski, P.J.³ Gebhard, I.⁴ Qualls, S.J.⁵ Wicnienski, N.A.⁶ Kelly, R.C.⁷

53
- 0005269941
- M. R. C. Gerstenberger A. Haas Angew. Chem., Int. Ed. Engl. 1981 20 647 667
- (1981) Angew. Chem., Int. Ed. Engl. , vol.20 , pp. 647-667
- Gerstenberger, M.R.C.¹ Haas, A.²

54
- 0000468774
- G. S. Lal G. P. Pez R. G. Syvret Chem. Rev. 1996 96 1737 1755
- (1996) Chem. Rev. , vol.96 , pp. 1737-1755
- Lal, G.S.¹ Pez, G.P.² Syvret, R.G.³

55
- 11144341001
- J.-A. Ma D. Cahard Chem. Rev. 2004 104 6119 6146
- (2004) Chem. Rev. , vol.104 , pp. 6119-6146
- Ma, J.-A.¹ Cahard, D.²

56
- 34547677638
- J.-A. Ma D. Cahard J. Fluorine Chem. 2007 128 975 996
- (2007) J. Fluorine Chem. , vol.128 , pp. 975-996
- Ma, J.-A.¹ Cahard, D.²

57
- 11844262714
- 2)
- P. T. Nyffeler S. G. Durón M. D. Burkart S. P. Vincent C.-H. Wong Angew. Chem., Int. Ed. 2005 44 192 212
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 192-212
- Nyffeler, P.T.¹ Durón, S.G.² Burkart, M.D.³ Vincent, S.P.⁴ Wong, C.-H.⁵

58
- 0027244913
- S.-H. Chen C. Fairchild S. W. Mamber V. Farina J. Org. Chem. 1993 58 2927 2928
- (1993) J. Org. Chem. , vol.58 , pp. 2927-2928
- Chen, S.-H.¹ Fairchild, C.² Mamber, S.W.³ Farina, V.⁴

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.