SCOPUS 정보 검색 플랫폼

Volumn 8, Issue 2, 2001, Pages 121-133

Syntheses and antitumor activities of potent inhibitors of ribonucleotide reductase: 3-amino-4-methylpyridine-2-carboxaldehyde-thiosemicarbazone (3-Amp), 3-amino-pyridine-2-carboxaldehyde-thiosemicarbazone (3-Ap) and its water-soluble prodrugs

(5) Li, J a Zheng, L M a King, I a Doyle, T W a Chen, S H a

a ELI LILLY AND COMPANY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINO 4 METHYLPYRIDINE 2 CARBOXALDEHYDE THIOSEMICARBAZONE; 3 AMINO PYRIDINE 2 CARBOXALDEHYDE THIOSEMICARBAZONE; ALKALINE PHOSPHATASE; DEOXYRIBONUCLEOTIDE; DISULFIDE; ENZYME INHIBITOR; GEMCITABINE; GLUTATHIONE; HEME; IRON; NUCLEOSIDE ANALOG; PALLADIUM; PHOSPHATE; PICOLINE DERIVATIVE; PRODRUG; PROTEIN; RADICAL; RIBONUCLEOTIDE; RIBONUCLEOTIDE REDUCTASE; TEZACITABINE; THIOL DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING AFFINITY; BIOTRANSFORMATION; CELL DIVISION; CHEMICAL REACTION; DNA SYNTHESIS; DRUG ACTIVITY; DRUG BINDING; DRUG EFFICACY; DRUG SAFETY; DRUG SOLUBILITY; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME BINDING; ENZYME SUBUNIT; IN VIVO STUDY; LUNG CARCINOMA; LUNG NON SMALL CELL CANCER; MAMMAL CELL; MELANOMA; MOUSE; NONHUMAN; PANCREAS CANCER; REDUCTION; SOLID TUMOR; XENOGRAFT;

EID: 0035036499 PISSN: 09298673 EISSN: None Source Type: Journal
DOI: 10.2174/0929867013373741 Document Type: Article

Times cited : (85)

References (48)

1
- 85037411980
- In Inhibitors of Ribonucleotide Diphosphate Reductase Activity, International Encyclopedia of Pharmacology and Therapeutics, Cory, J.G.; Cory, A.H. Eds.; Pergamon Press: New York, Section 128
- (1989) , pp. 1-16
- Cory, J.G.¹

2
- 0014962872
- (1970) J. Biol. Chem. , vol.245 , pp. 5228
- Elford, H.L.¹ Freese, M.² Passamani, E.³ Morris, H.P.⁴

3
- 0003517904
- In Inhibitors of Ribonucleotide Diphosphate Reductase Activity, International Encyclopedia of Pharmacology and Therapeutics, Cory, J.G.; Cory, A.H. Eds.; Pergamon Press: New York, Section 128
- (1989) , pp. 245-264
- Cory, J.G.¹ Chiba, P.²

4
- 0020541188
- (1983) Science , vol.221 , pp. 514
- Reichard, P.¹ Ehrenberg, A.²

5
- 0025737572
- (1991) J. Med. Chem. , vol.34 , pp. 1879
- Baker, C.H.¹ Banzon, J.² Bollinger, J.M.³ Stubbe, J.⁴ Samano, V.⁵ Robins, M.J.⁶ Lippert, B.⁷ Jarvi, E.⁸ Resvick, R.⁹

6
- 0005066666
- (27 Meet.)
- (1991) Proc. Am. Soc. Clin. Oncol. , vol.10 , pp. 143
- Casper, E.S.¹ Green, M.R.² Brown, T.D.³ Kelsen, D.P.⁴ Kresek, T.⁵ Trochanowski, B.⁶

7
- 0005088381
- In Design, Synthesis, and Antitumor Activity of An Inhibitor of Ribonucleotide Reductase, Weiner, D.B.; Williams, W.V. Eds.; CRC Press:Boca Raton, and the references cited therein.
- (1994) , pp. 3-34
- McCarthy, J.R.¹ Sunkara, P.S.²

8
- 0003314351
- Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J. R.; Welch, J. T. Eds.; ACS Symposium Series 639
- (1996) , pp. 246-264
- McCarthy, J.R.¹ Sunkara, P.² Mattews, D.P.³ Bitonti, A.J.⁴ Javi, E.T.⁵ Sabol, J.S.⁶ Resvick, R.J.⁷ Huber, E.W.⁸ van der Donk, W.A.⁹ Yu, G.¹⁰ Stubbe, J.¹¹

9
- 0025602528
- (1990) Biochem. Cell Biol. , vol.68 , pp. 1364
- Wright, J.A.¹ Chan, A.K.² Choy, B.K.³ Hurta, R.A.R.⁴ McClarty, G.A.⁵ Tagger, A.Y.⁶

10
- 0027934897
- (1994) Biochem. Pharm. , vol.48 , pp. 335
- Cory, J.G.¹ Cory, A.H.² Rappa, G.³ Lorico, A.⁴ Lin, M.-C.⁵ Sartorelli, A.C.⁶

11
- 0026666125
- (1992) J. Med. Chem. , vol.35 , pp. 3672
- Liu, M.-C.¹ Lin, T.-S.² Sartorelli, A.C.³

12
- 0028827448
- (1995) J. Med. Chem. , vol.38 , pp. 4234
- Liu, M.-C.¹ Lin, T.-S.² Penketh, P.³ Sartorelli, A.C.⁴

13
- 0029890537
- (1996) J. Med. Chem. , vol.39 , pp. 2586
- Liu, M.-C.¹ Lin, T.-S.² Cory, J.G.³ Cory, A.H.⁴ Sartorelli, A.C.⁵

14
- 0015362471
- (1972) Cancer Res. , vol.32 , pp. 1455
- DeConti, R.C.¹ Toftness, B.R.² Agrawal, K.C.³ Tomchick, R.⁴ Mead, J.A.R.⁵ Bertino, J.R.⁶ Sartorelli, A.C.⁷ Creasey, W.A.⁸

15
- 0015028544
- (1971) Cancer Res. , vol.31 , pp. 235
- Moore, E.C.¹ Booth, B.A.² Sartorelli, A.C.³

16
- 0026645975
- (1992) J. Med. Chem. , vol.35 , pp. 3667
- Wang, Y.¹ Liu, M.-C.² Lin, T.-S.³ Sartorelli, A.C.⁴

17
- 0032482306
- (1998) Tetrahedron , vol.54 , pp. 6311
- Niu, C.¹ Li, J.² Doyle, T.W.³ Chen, S.H.⁴

18
- 84943950090
- (1991) Pure Appl. Chem. , vol.63 , pp. 419
- Suzuki, A.¹

19
- 2042507954
- (1995) Chem. Rev. , vol.95 , pp. 2457
- Miyaura, N.¹ Suzuki, A.²

20
- 5244267486
- (1996) J. Org. Chem. , vol.61 , pp. 3017
- Riesgo, E.C.¹ Jin, X.² Thummei, R.P.³

21
- 0030068857
- (1996) J. Med. Chem. , vol.39 , pp. 304
- Atwal, K.S.¹ Ferrara, F.N.² Ding, C.Z.³ Grover, G.J.⁴ Sleph, P.G.⁵ Dzwonczyk, S.⁶ Baird, A.J.⁷ Normandin, D.E.⁸

22
- 0001722739
- (1973) Org. React. , vol.20 , pp. 455
- Porter, H.K.¹

23
- 0005100602
- Palladium Reagents in Organic Synthesis; Academic Press: San Diego, USA, Chapter 6.
- (1985)
- Heck, R.F.¹

24
- 33847802782
- (1975) J. Org. Chem. , vol.40 , pp. 1083
- Dieck, H.A.¹ Heck, R.F.²

25
- 85037403720
- Contractor for GMP manufacturing of 3-AP: Penta Biothch. Inc., 353f Vintage Park Dr., Foster City, CA 94404. Contractor for radio-labeled 3-AP: ChemSyn. Lab. 13605W. 96th Terrace, Lenexa, Kansas 66215-1297.

26
- 84985570392
- Angew
- (1986) Chem. Int. Ed. , vol.25 , pp. 508
- Stille, J.K.¹

27
- 0026699017
- (1992) Synthesis , pp. 803
- Mitchell, T.N.¹

28
- 0005031255
- In Advances in Metal-Organic Chemistry, Liebeskind, L.S. Ed.; JAI Press
- (1995) , vol.5 , pp. 1
- Farina, V.¹ Roth, G.P.²

29
- 85037402196
- General experimental conditions used for in vivo evaluation against murine M-109 lung carcinoma and B16-F10 murine melanoma: Balb/c mice were subcutaneously injected in the right flank on Day 0 with 0.2 mL of a cell/mL suspension of M-109 or B16-F10 tumor cells which had been grown to log phase in culture, trypsin digested to separate, washed with PBS and reconstituted. Injections of equal molar amount of 3-AP (4.5 mpk) or (10 mpk), or vehicle control (10% DMSO in water) were given intraperitoneally to the mice twice on day 3 through day 7. Ten mice were used for each group. The size of the tumors were measured by a caliper on The body weight and mortality of animals were recorded twice per week until the end of each experiment.

30
- 85037414882
- The acute toxicity of 3-AP recorded in vivo varied slightly from experiment to experiment. This variation may be the result of the following factors: the age of animal used, the different batches of tumor batches of drug used and etc.

31
- 0027290772
- (1993) Bioorg. Med. Chem. Lett. , vol.3 , pp. 1761
- Ueda, Y.¹ Mikkilineni, A.B.² Knipe, J.O.³ Rose, W.C.⁴ Casazza, A.M.⁵ Vyas, D.M.⁶

32
- 0027282618
- (1993) J. Pharm. Res. , vol.10 , pp. 1350
- Safadi, M.¹ Oliyai, R.² Stella, V.³

33
- 0030572491
- (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 1837
- Golik, J.¹ Wong, H.S.L.² Chen, S.H.³ Doyle, T.W.⁴ Wright, J.J.K.⁵ Knope, J.⁶ Rose, W.C.⁷ Casazza, A.M.⁸ Vyas, D.M.⁹

34
- 0028029894
- (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 2567
- Saulnier, M.G.¹ Langley, D.R.² Kadow, J.F.³ Senter, P.D.⁴ Knipe, J.O.⁵ Tun, M.M.⁶ Vyas, D.M.⁷ Doyle, T.W.⁸

35
- 0024342789
- (1989) J. Antibiot. , vol.42 , pp. 1199
- Vyas, D.M.¹ Benigni, D.² Rose, W.C.³ Bradner, W.T.⁴ Doyle, T.W.⁵

36
- 0005032480
- (1986) Cancer Res. , vol.46 , pp. 2848
- Russo, A.¹ DeGraff, W.² Friedman, N.³ Mitchell, J.B.⁴

37
- 0002729573
- Recent Advances in Chemotherapy, Ishigami, J. Eds.; University of Tokyo Press
- (1985) , pp. 485-486
- Vyas, D.M.¹ Chiang, Y.² Rose, W.C.³ Bradner, W.T.⁴ Doyle, T.W.⁵

38
- 0022617140
- (1986) J. Med. Chem. , vol.29 , pp. 84
- Lin, T.-S.¹ Wang, L.² Antonini, I.³ Cosby, L.A.⁴ Shiba, D.A.⁵ Kirkpatrick, L.⁶ Sartorelli, A.C.⁷

39
- 0025088074
- (1990) J. Org. Chem. , vol.55 , pp. 2975
- Senter, P.D.¹ Pearce, W.E.² Greenfield, R.S.³

40
- 0020385239
- (1982) Helv. Chem. Acta. , vol.65 , pp. 1837
- Haefliger, W.¹ Kloppner, E.²

41
- 0000841249
- (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 655
- Shipps, G.W.¹ Spitz, U.P.² Rebek, J.³

42
- 0030598098
- (1996) Tetrahedron , vol.52 , pp. 10113
- Jeffery, T.¹

43
- 0030047044
- (1996) Tetrahedron Lett. , vol.37 , pp. 771
- Siverberg, L.J.¹ Dillon, J.L.² Vemishetti, P.³

44
- 0002834242
- (1945) J. Chem. Soc. , pp. 381
- McCombie, H.¹ Saunders, B.C.² Stancey, G.J.³

45
- 0001141466
- (1994) J. Org. Chem. , vol.59 , pp. 6687
- Chao, H.-G.¹ Bernatowicz, M.S.² Reiss, P.D.³ Matsueda, G.R.⁴

46
- 0005100604
- (1999) Proc. Am. Assoc. Cancer Res. , vol.40 , pp. 301
- Li, Z.¹ Luo, X.² Chen, S.H.³ Li, X.Y.⁴ Li, J.⁵ Niu, C.⁶ Karra, S.⁷ Wang, Q.⁸ Barrow, S.⁹ Mao, J.¹⁰ Doyle, T.W.¹¹ King, I.¹² Zheng, L.-M.¹³

47
- 0032542001
- (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 3159
- Li, J.¹ Luo, X.² Wang, Q.³ Zheng, L.-M.⁴ King, I.⁵ Doyle, T.W.⁶ Chen, S.H.⁷

48
- 0029926683
- (1996) Tetrahedron , vol.52 , pp. 5591
- Mchand-Brynaert, J.¹ Bouchert, M.² Touillaux, R.³ Beaure, C.⁴ Fastrez, J.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.