Synthesis and antitumor activity of cholest-4α-methyl-7-en-3β-ol derivatives

Steroids

Volumn 71, Issue 6, 2006, Pages 476-483

  He, Lan ^a   Liu, Yumei ^a   Shi, Jiangong ^b   Pei, Qiang ^a  

^a BEIJING NORMAL UNIVERSITY   (China)

^b PEKING UNION MEDICAL COLLEGE   (China)

Author keywords

Antitumor activity; Cholest 4 methyl 7 en 3 ol; Structural modification

Indexed keywords

2 BENZYLIDENE CHOLEST 4ALPHA METHYL 7 EN 3 ONE; 2 HYDROXYARYL CHOLEST 4ALPHA METHYL 7 EN 3 ONE; 2 HYDROXYMETHYLENE CHOLEST 4ALPHA METHYL 7 EN 3 ONE; 2' PHENYL CHOLEST 4ALPHA METHYL 7 EN[3,2 C]PYRAZOLE; CHOLEST 4ALPHA METHYL 7 EN 3 ONE; CHOLEST 4ALPHA METHYL 7 EN 3ALPHA ETHINYL 3BETA OL; CHOLEST 4ALPHA METHYL 7 EN 3ALPHA ETHYLACETOXY 3BETA OL; CHOLEST 4ALPHA METHYL 7 EN 3ALPHA OL; CHOLEST 4ALPHA METHYL 7 EN 3BETA ETHINYL 3ALPHA OL; CHOLEST 4ALPHA METHYL 7 EN 3BETA OL; CHOLEST 4ALPHA METHYL 7 EN 3BETA OL 2 BUTENOATE; CHOLEST 4ALPHA METHYL 7 EN 3BETA OL ACETATE; CHOLEST 4ALPHA METHYL 7 EN 3BETA OL HEMIADIPATE; CHOLEST 4ALPHA METHYL 7 EN 3BETA OL HEMISUCCINATE; CHOLEST 4ALPHA METHYL 7 EN[3,2 C]PYRAZOLE; CHOLEST 4ALPHA METHYL 7,14 DIEN 3BETA OL; CHOLEST 4ALPHA METHYL 7,14 DIEN BETA OL ACETATE; CHOLEST 4ALPHA METHYL 8 EN 3BETA,7ALPHA DIOL; CHOLEST 4ALPHA METHYL 8 EN 7ALPHA ACETOXY 3 ONE; CHOLEST 4ALPHA METHYL 8 EN 7ALPHA ACETOXY 3BETA OL; CHOLEST 4ALPHA METHYL 8 EN 7ALPHA ETHOXY 3BETA OL; CHOLEST 4ALPHA METHYL 8 EN 7ALPHA ETHOXY 3BETA OL ACETATE; STEROL DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; COLON CANCER; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; LIVER CANCER; NASOPHARYNX CANCER; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CHOLESTEROL; DRACAENA; ESTERS; HELA CELLS; HUMANS; INHIBITORY CONCENTRATION 50; ISOMERISM; PLANT EXTRACTS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33646145745     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2006.01.006     Document Type: Article

References (12)

1. 7-cholesten-3β-ol-a link in sterol biogenesis. J Am Chem Soc 80 (1958) 6284-6292
2. Benjamin G., Gbongue A., Adima A., and Yoichiro L. Chemical analysis of the seed of the ripe fruit of Tieghemella heckelii. J Liquid Chromatogr Relat Technol 25 (2002) 2873-2882
3. Stonik V.A., Ponomarenko L.P., Makarieva T.N., Boguslavsky V.M., and Dmitrenok A.S. Free sterol compositions from the sea cucumbers Pseudostichopus trachus, Holothuria (Microtele) nobilis, Holothuria scabra, Trochostoma orientale and Bathyplotes natans. Comp Biochem Physiol B Biochem Mol Biol 120B (1998) 337-347
4. Raederstorff D., and Rohmer M. Sterol biosynthesis via cycloartenol and other biochemical features related to photosynthetic phyla in the amebae Naegleria lovaniensis and Naegleria gruberi. Eur J Biochem 164 (1987) 427-434
5. Shen X.M., Liu Y.M., and He L. Structure and properties of cholest-4α-methyl-8-en-3β,7α-diol diacetate. Chin J Chem 23 (2005) 305-309
6. Shen X.M., Wang Z.H., Chen C., Tu P.F., and He L. Zhong Cao Yao 35 (2004) 221-228
7. Carmichael J., degraff W.G., Gazdar A.F., Minna J.D., and Mitchell J.B. Evaluation of a tetrazolium-based semiautomated colorimetric assay: assessment of chemosensitivity testing. Cancer Res 47 (1987) 936-942
8. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65 (1983) 55-63
9. 7-stenols with selenium dioxide. J Am Chem Soc 75 (1953) 4404-4414
10. Linton R.O., Manson A.J., Stonner F.W.S., Neumann H.C., Christiansen R.G., Clarke R.L., et al. Steroidal[3,2-c]pyrazoles. Part II: androstanes, 19-norandrostanes and their unsaturated analogs. J Am Chem Soc 83 (1961) 1478-1491
11. Hirschmann R., Buchschacher P., Steinberg N.G., Fried J.H., Ellis R., Kent G., et al. Synthesis and structure of steroidal pregn-4-eno- and 5α-pregnano[3,2-c]pyrazole: a novel class of potent anti-inflammatory steroids. J Am Chem Soc 86 (1964) 1520-1527
12. Rapole K.R., Siddiqui A.H., Batta A.K., Rao S.J., Kumar P., and Salen G. Synthesis of steroidal pyrimidines. Synth Commun 26 (1996) 3511-3515