Novel coumarin derivatives of heterocyclic compounds as lipid-lowering agents

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 15, 2003, Pages 2547-2551

  Madhavan, Gurram R ^a   Balraju, Vadla ^a   Mallesham, Bejugam ^a   Chakrabarti, Ranjan ^a   Lohray, Vidya B ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1(2H) PHTHALAZINONE; 1H INDOLE; 2 BENZYLMALOIC ACID; 2 ETHOXY 3 PHENYLPROPANOIC ACID; 2 ETHYL 6 METHYL 4(3H) PYRIMIDINONE; 2 METHYL 4(3H) QUINAZOLINONE; 2 METHYLAMINOBENZOXAZOLE; 2 PHENYL 5 METHYLOXAZOLE; 6 METHYL 1(2H) PHTHALAZINONE; 9H PHENOXAZINE; ANTILIPEMIC AGENT; ANTIOXIDANT; COUMARIN DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FENOFIBRATE; HETEROCYCLIC COMPOUND; TRIACYLGLYCEROL; UNCLASSIFIED DRUG;

ANIMAL; ARTICLE; BLOOD; CHEMISTRY; CYCLIZATION; DRUG ACTIVITY; IN VIVO STUDY; MOUSE; SCREENING; SYNTHESIS;

EID: 0037971925     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00490-6     Document Type: Article

References (13)

1. La Rosa J.C., Hi J., Vupputuri S. J. Am. Med. Assoc. 282:1999;2340.
2. Evans M., Rees A. Curr. Opin. Lipidol. 13:2002;415.
3. Staels B., Dallongeville J., Auwerx J., Schoonjans K., Leitersdorf E., Fruchart J.C. Circulation. 98:1998;2088.
4. Balz F. Natural Antioxidants in Human Health and Disease. 1994;Acedamic Press, San Diego, CA.
5. Lohray B.B., Lohray V.B., Bajji A.C., Kalchar S., Poondra R.R., Padakanti S., Chakrabarthi R., Vikramidithyan R.K., Misra P., Juluri S., Mamidi N.V.S.R., Rajagopalan R. J. Med. Chem. 44:2001;2675.
6. Shirley D.A., Sen K., Glimer J.C. J. Org. Chem. 26:1961;3587.
7. (a) Hisashi S., Syoji O., Mashiro T., Tsutomu S., Megumi I., Korekiyo W., Itsuo U. J. Med. Chem. 41:1998;1927 (b) Buckle D.R., Cantello B.C.C., Cawthorne M.A., Coyle P.J., Dean D.K., Faller A., Haigh D., Hindley R.M., Jefcott L.J., Lister C.A., Pinto I.L., Rami H.K., Smith D.G., Smith S.A. Bioorg. Med. Chem. Lett. 6:1996;2127 (c) Lohray B.B., Vidya B., Rao P.B., Madhavan G.R., Murali N., Rao K.N., Reddy A.K., Rajesh B.M., Reddy P.G., Chakraborthy R., Vikramadithyan R.K., Rajagopalan R., Mamidi N.V.S.R., Jajoo H.K., Subramaniam S. J. Med. Chem. 41:1998;1619 (d) Csampai A., Koermendy K., Sohar P., Ruff F. Tetrahedron. 45:1989;5539 (e) Ranganathan D., Farooqui F., Mehrotra S., Kesavan K. Heterocycles. 24:1986;2493. and in house prepared.
8. (a) Hisashi S., Syoji O., Mashiro T., Tsutomu S., Megumi I., Korekiyo W., Itsuo U. J. Med. Chem. 41:1998;1927 (b) Buckle D.R., Cantello B.C.C., Cawthorne M.A., Coyle P.J., Dean D.K., Faller A., Haigh D., Hindley R.M., Jefcott L.J., Lister C.A., Pinto I.L., Rami H.K., Smith D.G., Smith S.A. Bioorg. Med. Chem. Lett. 6:1996;2127 (c) Lohray B.B., Vidya B., Rao P.B., Madhavan G.R., Murali N., Rao K.N., Reddy A.K., Rajesh B.M., Reddy P.G., Chakraborthy R., Vikramadithyan R.K., Rajagopalan R., Mamidi N.V.S.R., Jajoo H.K., Subramaniam S. J. Med. Chem. 41:1998;1619 (d) Csampai A., Koermendy K., Sohar P., Ruff F. Tetrahedron. 45:1989;5539 (e) Ranganathan D., Farooqui F., Mehrotra S., Kesavan K. Heterocycles. 24:1986;2493. and in house prepared.
9. (a) Hisashi S., Syoji O., Mashiro T., Tsutomu S., Megumi I., Korekiyo W., Itsuo U. J. Med. Chem. 41:1998;1927 (b) Buckle D.R., Cantello B.C.C., Cawthorne M.A., Coyle P.J., Dean D.K., Faller A., Haigh D., Hindley R.M., Jefcott L.J., Lister C.A., Pinto I.L., Rami H.K., Smith D.G., Smith S.A. Bioorg. Med. Chem. Lett. 6:1996;2127 (c) Lohray B.B., Vidya B., Rao P.B., Madhavan G.R., Murali N., Rao K.N., Reddy A.K., Rajesh B.M., Reddy P.G., Chakraborthy R., Vikramadithyan R.K., Rajagopalan R., Mamidi N.V.S.R., Jajoo H.K., Subramaniam S. J. Med. Chem. 41:1998;1619 (d) Csampai A., Koermendy K., Sohar P., Ruff F. Tetrahedron. 45:1989;5539 (e) Ranganathan D., Farooqui F., Mehrotra S., Kesavan K. Heterocycles. 24:1986;2493. and in house prepared.
10. (a) Hisashi S., Syoji O., Mashiro T., Tsutomu S., Megumi I., Korekiyo W., Itsuo U. J. Med. Chem. 41:1998;1927 (b) Buckle D.R., Cantello B.C.C., Cawthorne M.A., Coyle P.J., Dean D.K., Faller A., Haigh D., Hindley R.M., Jefcott L.J., Lister C.A., Pinto I.L., Rami H.K., Smith D.G., Smith S.A. Bioorg. Med. Chem. Lett. 6:1996;2127 (c) Lohray B.B., Vidya B., Rao P.B., Madhavan G.R., Murali N., Rao K.N., Reddy A.K., Rajesh B.M., Reddy P.G., Chakraborthy R., Vikramadithyan R.K., Rajagopalan R., Mamidi N.V.S.R., Jajoo H.K., Subramaniam S. J. Med. Chem. 41:1998;1619 (d) Csampai A., Koermendy K., Sohar P., Ruff F. Tetrahedron. 45:1989;5539 (e) Ranganathan D., Farooqui F., Mehrotra S., Kesavan K. Heterocycles. 24:1986;2493. and in house prepared.
11. (a) Hisashi S., Syoji O., Mashiro T., Tsutomu S., Megumi I., Korekiyo W., Itsuo U. J. Med. Chem. 41:1998;1927 (b) Buckle D.R., Cantello B.C.C., Cawthorne M.A., Coyle P.J., Dean D.K., Faller A., Haigh D., Hindley R.M., Jefcott L.J., Lister C.A., Pinto I.L., Rami H.K., Smith D.G., Smith S.A. Bioorg. Med. Chem. Lett. 6:1996;2127 (c) Lohray B.B., Vidya B., Rao P.B., Madhavan G.R., Murali N., Rao K.N., Reddy A.K., Rajesh B.M., Reddy P.G., Chakraborthy R., Vikramadithyan R.K., Rajagopalan R., Mamidi N.V.S.R., Jajoo H.K., Subramaniam S. J. Med. Chem. 41:1998;1619 (d) Csampai A., Koermendy K., Sohar P., Ruff F. Tetrahedron. 45:1989;5539 (e) Ranganathan D., Farooqui F., Mehrotra S., Kesavan K. Heterocycles. 24:1986;2493. and in house prepared.
12. Shin C., Nakajima Y., Sato Y. Chem. Lett. 1984;1301.
13. An inbreed colony (at our own animal house) of Swiss Albino Mice (SAM) of 21-29 g body weight, moderately hypertriglycerimic, has been used for screening the compounds. Animals (5 per group) were treated orally with 3 mg/kg/day of 5a-b, 7a-i, 8, 10a, 11a, 11c for 6 days. The control animals were treated with the vehicle (0.25% carboxymethyl cellulose, 3 mL/kg) only. Animals were bled through retro orbital sinus on day-1 and day-6 of the experiment. Plasma samples were prepared and triglyceride levels were measured by using a commercial kit (Pointe Scientific, USA). For calculating of percentage reduction of triglycerides, the standard method published previously (Reddy, K. A.; Lohray, B. B.; Reddy, A. S.; Mamidi, N. V. S. R.; Reddy, P. P.; Saibaba, V.; Jaipal Reddy, N.; Suryaprakash, A.; Misra, P.; Vikramidithyan, R. K.; Rajapopalan, R. J. Med. Chem. 1999, 42, 3265 and Saibal, K. D.; Krorrida, V. L. N.; Jagadhesan, H; Iqbal, J. Bioorg. Med. Chem. Lett., 2002, 12, 3579.) was applied.