Synthesis and structure-activity relationship of diarylamide derivatives as selective inhibitors of the proliferation of human endothelial cells

Bioorganic and Medicinal Chemistry

Volumn 10, Issue 11, 2002, Pages 3473-3480

  Ogita, Haruhisa ^a   Isobe, Yoshiaki ^a   Takaku, Haruo ^a   Sekine, Rena ^a   Goto, Yuso ^a   Misawa, Satoru ^a   Hayashi, Hideya ^a  

^a JAPAN ENERGY CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANGIOGENESIS INHIBITOR; AROMATIC AMIDE; N (2 ACETYL 4,5 DIMETHOXYPHENYL) 2 [4 [(PHENYLAMINO)CARBONYLAMINO]PHENYL]ETHANAMIDE; N (2 ACETYL 4,5 DIMETHOXYPHENYL) 3 [4 (2 PHENYLACETYLAMINO)PHENYL]PROPANAMIDE; N (2 ACETYL 4,5 DIMETHOXYPHENYL) 3 [4 (PHENOXYCARBONYLAMINO)PHENYL]PROPANAMIDE; N (2 ACETYL 4,5 DIMETHOXYPHENYL) 3 [4 (PHENYLCARBONYLAMINO)PHENYL]PROPANAMIDE; N (2 ACETYL 4,5 DIMETHOXYPHENYL) 3 [4 [(BENZYLAMINO)CARBONYLAMINO]PHENYL]PROPANAMIDE; N (2 ACETYL 4,5 DIMETHOXYPHENYL) 3 [4 [(BUTYLAMINO)CARBONYLAMINO]PHENYL]PROPANAMIDE; N (2 ACETYL 4,5 DIMETHOXYPHENYL) 3 [4 [(CYCLOHEXYLAMINO)CARBONYLAMINO]PHENYL]PROPANAMIDE; N (2 ACETYL 4,5 DIMETHOXYPHENYL) 3 [4 [(PHENYLAMINO)CARBONYLAMINO]PHENYL]PROP 2 ENAMIDE; N (2 ACETYL 4,5 DIMETHOXYPHENYL) 3 [4 [(PHENYLAMINO)CARBONYLAMINO]PHENYL]PROPANAMIDE; N (2 ACETYL 4,5 DIMETHOXYPHENYL) 3 [4 [[(2 AMINOPHENYL)AMINO]CARBONYLAMINO]PHENYL]PROPANAMIDE; N (2 ACETYL 4,5 DIMETHOXYPHENYL) 3 [4 [[(2 NITROPHENYL)AMINO]CARBONYLAMINO]PHENYL]PROPANAMIDE; N (2 ACETYL 4,5 DIMETHOXYPHENYL) 3 [4 [[(3 AMINOPHENYL)AMINO]CARBONYLAMINO]PHENYL]PROPANAMIDE; N (2 ACETYL 4,5 DIMETHOXYPHENYL) 3 [4 [[(3 NITROPHENYL)AMINO]CARBONYLAMINO]PHENYL]PROPANAMIDE; N (2 ACETYL 4,5 DIMETHOXYPHENYL) 3 [4 [[(3,4,5 TRIMETHOXYPHENYL)AMINO]CARBONYLAMINO]PHENYL]PROPANAMIDE; N (2 ACETYL 4,5 DIMETHOXYPHENYL) 3 [4 [[(4 ACETYLPHENYL)AMINO]CARBONYLAMINO]PHENYL]PROPANAMIDE; N (2 ACETYL 4,5 DIMETHOXYPHENYL) 3 [4 [[(4 AMINOPHENYL)AMINO]CARBONYLAMINO]PHENYL]PROPANAMIDE; N (2 ACETYL 4,5 DIMETHOXYPHENYL) 3 [4 [[(4 FLUOROPHENYL)AMINO]CARBONYLAMINO]PHENYL]PROPANAMIDE; N (2 ACETYL 4,5 DIMETHOXYPHENYL) 3 [4 [[(4 METHOXYPHENYL)AMINO]CARBONYLAMINO]PHENYL]PROPANAMIDE; N (2 ACETYL 4,5 DIMETHOXYPHENYL) 3 [4 [[(4 METHYLPHENYL)AMINO]CARBONYLAMINO]PHENYL]PROPANAMIDE; N (2 ACETYL 4,5 DIMETHOXYPHENYL) 3 [4 [[(4 NITROPHENYL)AMINO]CARBONYLAMINO]PHENYL]PROPANAMIDE; N (2 ACETYL 4,5 DIMETHOXYPHENYL) 3 [4 [[(4 PYRIDYL)AMINO]CARBONYLAMINO]PHENYL]PROPANAMIDE; N (2 ACETYL 4,5 DIMETHOXYPHENYL) 4 [4 [(PHENYLAMINO)CARBONYLAMINO]PHENYL]BUTANAMIDE; N (2 ACETYL 4,5 DIMETHOXYPHENYL)[4 [(PHENYLAMINO)CARBONYLAMINO]PHENYL]FORMAMIDE; TRANILAST; UNCLASSIFIED DRUG;

ANGIOGENESIS; ARTICLE; CELL PROLIFERATION; CONTROLLED STUDY; CORONARY ARTERY; DRUG ACTIVITY; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; ENDOTHELIUM CELL; HUMAN; HUMAN CELL; SMOOTH MUSCLE FIBER; STRUCTURE ACTIVITY RELATION;

AMIDES; ANGIOGENESIS INHIBITORS; CELL DIVISION; DNA; ENDOTHELIUM, VASCULAR; HUMANS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MUSCLE, SMOOTH, VASCULAR; STRUCTURE-ACTIVITY RELATIONSHIP; UMBILICAL VEINS;

EID: 0036836831     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(02)00258-4     Document Type: Article

References (17)

1. Azuma H., Banno K., Yoshimura T. Br. J. Pharmacol. 8:1976;483
2. Suzawa H., Kikuchi S., Arai N., Koda A. Jpn. J. Pharmacol. 60:1992;91
3. Suzawa H., Kikuchi S., Ichikawa K., Koda A. Jpn. J. Pharmacol. 60:1992;85.
4. Isaji, M.; Miyata, H.; Ajisawa, Y. PCT Patent Publication, WO 97/29744.
5. Isaji, M.; Miyata, H.; Ajisawa, Y.; Yoshimura, N. Br. J. Pharmacol. 1997, 122, 1061
6. Timar J., Dome D., Fazakas K., Janovics A., Paku S. Pathol. Oncol. Res. 7:2001;85.
7. Ogita H., Isobe Y., Takaku H., Sekine R., Goto Y., Misawa S., Hayashi H. Bioorg. Med. Chem. Lett. 11:2001;549
8. Ogita H., Isobe Y., Takaku H., Sekine R., Goto Y., Misawa S., Hayashi H. Bioorg. Med. Chem. 10:2002;1865.
9. Kandel J., Bossy-Wetzel E., Radvanyi F., Klagsbrun M., Folkman J., Hanahan D. Cell. 66:1991;1095
10. Pepper M.S., Belin D., Montesano R., Orci L., Vassalli J.D. J. Cell. Biol. 111:1990;743
11. Bussolino F., Di Renzo M.F., Ziche M., Bocchietto E., Olivero M., Naldini L., Gaudino G., Tamagnone L., Coffer A., Comoglio P.M. J. Cell. Biol. 119:1992;629.
12. Ferrara N., Davis-Smyth T. Endocr. Rev. 18:1997;4.
13. Kubo, K.; Shimizu, T.; Ohyama, S.; Murooka, H.; Nishitoba, T.; Kato, S.; Kobayashi, Y.; Yagi, M.; Isoe, T.; Nakamura, K.; Osawa, T.; Izawa, T. Bioorg. Med. Chem. Lett. 1997, 7, 2935.
14. Kubo, K.; Shimizu, T.; Ohyama, S. PCT Patent Publication, WO 97/17329.
15. Kubo, K.; Fujiwara, Y.; Isoe, T. PCT Patent Publication, WO 00/43366.
16. Kubo, K.; Fujiwara, Y.; Iwakubo, M.; Murooka, H.; Iwai, A.; Nakamura, K.; Hasegawa, K.; Kobayashi, Y.; Takahashi, N.; Takahashi, K.; Shibuya, M.; Osawa, T.; Isoe T. Am. Assoc. Cancer Res. 2002, 43, 182 (abstract 913).
17. Isaji M., Miyata H., Ajisawa Y., Yoshimura N. Br. J. Pharmacol. 127:1997;537.