Synthesis of potential pregnenolone and progesterone spin probes for biomembranes and immunoassays

被引：12

作者：

Katoch, R ^{[1
]}

Korde, SS ^{[1
]}

Deodhar, KD ^{[1
]}

Trivedi, GK ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

来源：

TETRAHEDRON | 1999年 / 55卷 / 06期

关键词：

D O I：

10.1016/S0040-4020(98)01187-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis and characterization of four new steroidal spin labels, viz., 3'-[[(pregn-5-en-3 beta-ol-20S-yl)methyl]oate]- 2',2',5',5'-tetramethylpyrrolidine-1'-oxyl,3'-[[(pregn-4-en-3- one-20S-yl)methyl]oate]-2',2',5'.5'-tetra methyl pyrrolidine-1'-oxyl, 3 "[(3 beta-acetoxypregn-5-en-20-one-16 alpha-yl)prop-2'xi-ol-3'xi-oate]-2 ",2 ",5 ",5 "-tetramethyl pyrrolidine-1 "-oxyl and 3 "-[(pregn-5-en-3,20-dione-16 alpha-yl)prop-2'xi-ol-3'xi-oate]-2',2',5',5'-tetramethylpyrrolidine-1'-oxyl has been described which involves functionalization of the parent hormone at C-20 and C-16. The key step to all the products was the condensation of 3-carboxyproxyl with the derivatized synthons. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1741 / 1754

页数：14

共 20 条

[1]

AUZOU G, 1988, Steroids, V51, P465, DOI 10.1016/0039-128X(88)90045-1

[2] SYNTHESES OF POTENTIAL SPIN PROBES FOR BIOMEMBRANES - TEMPO AND PROXYL NITROXIDES OF LITHOCHOLIC ACID [J].

BANERJEE, S ;

TRIVEDI, GK .

TETRAHEDRON, 1992, 48 (45) :9939-9950

[3] 2'-(3-ALPHA-BENZYLOXY-24-NORCHOLAN-23-YL)-2',4',4'-TRIMETHYL-4',5'-DIHYDROOXAZOLINE-N-OXYL AS A POTENTIAL SPIN-PROBE FOR MODEL MEMBRANES [J].

BANERJEE, S ;

TRIVEDI, GK ;

SRIVASTAVA, S ;

PHADKE, RS .

STEROIDS, 1994, 59 (06) :377-382

[4] SYNTHESIS OF 2'-(3-ALPHA-BENZYLOXY-24-NORCHOLAN-23-YL)-2',4',4'-TRIMETHYL-4',5'-DIHYDROOXAZOLINE-N-OXYL - A NEW POTENTIAL SPIN PROBE FOR BIOMEMBRANES [J].

BANERJEE, S ;

DESAI, UR ;

TRIVEDI, GK .

TETRAHEDRON, 1992, 48 (01) :133-148

[5]

Banerjee S, 1993, Bioorg Med Chem, V1, P341, DOI 10.1016/S0968-0896(00)82140-9

[6]

CAIRNS J, 1977, J CHEM SOC P1, P1558

[7] STEROID STRUCTURE AND FUNCTION .2. CONFORMATIONAL TRANSMISSION AND RECEPTOR-BINDING OF MEDROXYPROGESTERONE ACETATE [J].

DUAX, WL ;

CODY, V ;

GRIFFIN, J ;

HAZEL, J ;

WEEKS, CM .

JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, 1978, 9 (10) :901-907

[8] A SYNTHESIS OF 7-ALPHA-SUBSTITUTED ESTRADIOLS - SYNTHESIS AND BIOLOGICAL EVALUATION OF A 7-ALPHA-PENTYL SUBSTITUTED BODIPY FLUORESCENT CONJUGATE AND A F-18 LABELED 7-ALPHA-PENTYLESTRADIOL ANALOG [J].

FRENCH, AN ;

WILSON, SR ;

WELCH, MJ ;

KATZENELLENBOGEN, JA .

STEROIDS, 1993, 58 (04) :157-169

[9] UBER STEROIDE UND SEXUALHORMONE .188. EINE NEUE VARIANTE DER SYNTHESE DES BIOLOGISCH HOCH AKTIVEN GESTAGENS 17-ALPHA-METHYL-PROGESTERON [J].

GUNTHARD, HH ;

BERIGER, E ;

ENGEL, CR ;

HEUSSER, H .

HELVETICA CHIMICA ACTA, 1952, 35 (07) :2437-2444

[10] STERISCHE EINFLUSSE EINER 16ALPHA-METHYLGRUPPE AUF REAKTIONEN IN DER SEITENKETTE VON ALLOPREGNAN-VERBINDUNGEN - UBER STEROIDE .159. [J].

HEUSLER, K ;

KEBRLE, J ;

MEYSTRE, C ;

UEBERWASSER, H ;

WIELAND, P ;

ANNER, G ;

WETTSTEIN, A .

HELVETICA CHIMICA ACTA, 1959, 42 (06) :2043-2062

← 1 2 →