Synthesis and evaluation of carbamate prodrugs of a phenolic compound

Chemical and Pharmaceutical Bulletin

Volumn 55, Issue 2, 2007, Pages 328-333

  Igarashi, Yasushi ^a,c   Yanagisawa, Erika ^a   Ohshima, Toshihiro ^a   Takeda, Shuichi ^a   Aburada, Masaki ^b   Miyamoto, Ken Ichi ^c  

^a TSUMURA AND CO   (Japan)

^b MUSASHINO UNIVERSITY   (Japan)

^c KANAZAWA UNIVERSITY   (Japan)

Author keywords

Capillarisin; Carbamate; Prodrug

Indexed keywords

2 [[4 (CARBANILOXY)PHENYL]THIO] 7 ISOPROPOXY 5,6 DIMETHOXY 4H CHROMEN 4 ONE; 2 [[4 [(ETHYLCARBAMOYL)OXY]PHENYL]THIO] 7 ISOPROPOXY 5,6 DIMETHOXY 4H CHROMEN 4 ONE; 2 [[4 [[(2 CHLOROETHYL)CARBAMOYL]OXY]PHENYL]THIO] 7 ISOPROPOXY 5,6 DIMETHOXY 4H CHROMEN 4 ONE; 2 [[4 [[(2 HYDROXYETHYL)METHYLCARBAMOYL]OXY]PHENYL]THIO] 7 ISOPROPOXY 5,6 DIMETHOXY 4H CHROMEN 4 ONE; 2 [[4 [[(3 HYDROXYPROPYL)METHYLCARBAMOYL]OXY]PHENYL]THIO] 7 ISOPROPOXY 5,6 DIMETHOXY 4H CHROMEN 4 ONE; 2 [[4 [[(4 HYDROXYPIPERIDINO)CARBONYL]OXY]PHENYL]THIO] 7 ISOPROPOXY 5,6 DIMETHOXY 4H CHROMEN 4 ONE; 2 [[4 [[[2 (HYDROXYMETHYL) 1 PYROLIDINYL]CARBONYL]OXY]PHENYL]THIO] 7 ISOPROPOXY 5,6 DIMETHOXY 4H CHROMEN 4 ONE; 2 [[4 [[BIS(2 HYDROXYETHYL)CARBAMOYL]OXY]PHENYL]THIO] 7 ISOPROPOXY 5,6 DIMETHOXY 4H CHROMEN 4 ONE; 2 [[[4 (DIMETHYLCARBAMOYL)OXY]PHENYL]THIO] 7 ISOPROPOXY 5,6 DIMETHOXY 4H CHROMEN 4 ONE; 7 ISOPROPOXY 2 [[4 [(ISOPROPYLCARBAMOYL)OXY]PHENYL]THIO] 5,6 DIMETHOXY 4H CHROMEN 4 ONE; 7 ISOPROPOXY 5,6 DIMETHOXY 2 [4 [(METHYLPHENYLCARBAMOYL)OXY]PHENYL]THIO 4H CHROMEN 4 ONE; 7 ISOPROPOXY 5,6 DIMETHOXY 2 [[4 [(METHOXYMETHYCARBAMOYL)OXY]PHENYL]THIO] 4H CHROMEN 4 ONE; 7 ISOPROPOXY 5,6 DIMETHOXY 2 [[4 [(METHYLCARBAMOYL)OXY]PHENYL]THIO] 4H CHROMEN 4 ONE; 7 ISOPROPOXY 5,6 DIMETHOXY 2 [[4 [(MORPHORINOCARBONYL)OXY]PHENYL]THIO] 4H CHROMEN 4 ONE; 7 ISOPROPOXY 5,6 DIMETHOXY 2 [[4 [(PROPYLCARBAMOYL)OXY]PHENYL]THIO] 4H CHROMEN 4 ONE; 7 ISOPROPOXY 5,6 DIMETHOXY 2 [[4 [[(2 METHOXYETHYL)METHYLCARBAMOYL]OXY]PHENYL]THIO] 4H CHROMEN 4 ONE; 7 ISOPROPOXY 5,6 DIMETHOXY 2 [[4 [[(4 METHYL 1 PIPERAZINYL)CARBONYL]OXY]PHENYL]THIO] 4H CHROMEN 4 ONE; 7 ISOPROPOXY 5,6 DIMETHOXY 2 [[4 [[[2 (METHOXYMETHYL) 1 PYRROLIDINYL]CARBONYL]OXY]PHENYL]THIO] 4H CHROMEN 4 ONE; 7 ISOPROPOXY 5,6 DIMETHOXY 2 [[4 [[METHYL(2 PYRIDYL)CARBAMOYL]OXY]PHENYL]THIO] 4H CHROMEN 4 ONE; [[[4 [(7 ISOPROPOXY 5,6 DIMETHOXY 4 OXO 4H CHROMEN 2 YL)THIO]PHENOXY]CARBONYL]IMINO]DIACETONITRILE; [[[4 [(7 ISOPROPOXY 5,6 DIMETHOXY 4 OXO 4H CHROMEN 2 YL)THIO]PHENOXY]CARBONYL]METHYLAMINO]ACETIC ACID; [[[4 [(7 ISOPROPOXY 5,6 DIMETHOXY 4 OXO 4H CHROMEN 2 YL)THIO]PHENOXY]CARBONYL]METHYLAMINO]ACETONITRILE; CAPILLARISIN; CARBAMIC ACID DERIVATIVE; DIETHYL[[[4 [(7 ISOPROPOXY 5,6 DIMETHOXY 4 OXO 4H CHROMEN 2 YL)THIO]PHENOXY]CARBONYL]IMINO]DIACETATE; ETHYL[[[4 [(7 ISOPROPOXY 5,6 DIMETHOXY 4 OXO 4H CHROMEN 2 YL)THIO]PHENOXY]CARBONYL]AMINO]PROPIONATE; METHYL N [[4 [(7 ISOPROPOXY 5,6 DIMETHOXY 4 OXO 4H CHROMEN 2 YL)THIO]PHENOXY]CARBONYL]METHIONATE; N [[4 [(7 ISOPROPOXY 5,6 DIMETHOXY 4 OXO 4H CHROMEN 2 YL)THIO]PHENOXY]CARBONYL]PROLINE; PHENOL DERIVATIVE; PRODRUG; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; BIOTRANSFORMATION; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG DETERMINATION; DRUG SCREENING; DRUG SYNTHESIS; IN VIVO STUDY; MALE; NONHUMAN; RAT;

ADMINISTRATION, ORAL; ANIMALS; BIOTRANSFORMATION; CARBAMATES; DRUG STABILITY; MODELS, CHEMICAL; PHENOLS; PRODRUGS; RATS;

EID: 33846946864     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.55.328     Document Type: Article

References (14)

1. Komiya T., Tsukui M., Oshio H., Chem. Pharm. Bull., 23, 1387-1388 (1975).
2. Igarashi Y., Kumazawa H., Ohshima T., Satomi H., Terabayashi S., Takeda S., Aburada M., Miyamoto K., Chem. Pharm. Bull., 53, 1088-1091 (2005).
3. Igarashi Y., Yamaguchi T., Ogawa Y., Tomita M., Hayashi H., Sato T., Hosaka K., WO 9209594 (1992).
4. Nagamura S., Kanda Y., Kobayashi E., Gomi K., Saito H., Chem. Pharm. Bull., 43, 1530-1535 (1995).
5. Sawada S., Okajima S., Aiyama R., Nokata K., Furuta T., Yokokura T., Sugino E., Yamaguchi K., Miyasaka T., Chem. Pharm. Bull., 39, 1446-1454 (1991).
6. Savolainen J., Leppanen J., Forsberg M., Taipale H., Nevalainen T., Huuskonen J., Gynther J., Mannisto P. T., Jarvinen T., Life Sci., 67, 205-216 (2000).
7. Thorberg S., Berg S., Lundstrom J., Petterson B., Wijkstrom A., Sanchez D., Lindberg P., Nilsson L. G., J. Med. Chem., 30, 2008-2012 (1987).
8. Hosokawa M., Imai T., Farumashia, 37, 119-123 (2001).
9. Yoon K. J. P., Morton C. L., Potter P. M., Danks M. K., Lee R. E., Bioorg. Med. Chem., 11, 3237-3244 (2003).
10. Lindberg C., Roos C., Tunek A., Svensson L. A., Drug Metab. Dispos., 17, 311-322 (1989).
11. Hansen K. T., Faarup P., Bundgaard H., J. Pharm. Sci., 80, 793-798 (1991).
12. Saari W. S., Schwering J. E., Lyle P. A., Smith S. J., Engelhardt E. L., J. Med. Chem., 33, 97-101 (1990).
13. Shan D., Nicolaou M. G., Borchardt R. T., Wang B., J. Pharm., Sci., 86, 765-767 (1997).
14. Sohma Y., Hayashi Y., Ito T., Matsumoto H., Kimura T., Kiso Y., J. Med. Chem., 46, 4124-4135 (2003).