Synthesis of Several 5α-Androstano[17,16-d]Pyrazolines from Tigogenin

被引:7
作者
Nadaraia, N. Sh. [1 ]
Kakhabrishvili, M. L. [1 ]
Onashvili, E. O. [1 ]
Barbakadze, N. N. [1 ]
Getia, M. Z. [1 ,2 ]
Pichette, A. [2 ]
Sikharulidze, M. I. [1 ]
Makhmudov, U. S. [3 ]
机构
[1] Tbilisi State Med Univ, I Kutateladze Inst Pharmaceut Chem, GE-0159 Tbilisi, Georgia
[2] Univ Quebec Chicoutimi, LASEVE, Chicoutimi, PQ G7H 2B1, Canada
[3] Uzbek Acad Sci, S Yu Yunusov Inst Chem Plant Subst, Tashkent, Uzbekistan
关键词
synthesis; 5; alpha-steroids; hydrazines; hydrazones; cyclization; pyrazolines;
D O I
10.1007/s10600-014-1151-1
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
New androstanopyrazolines and hydrazones were synthesized via acid-catalyzed condensation of the tigogenin transformation product 5 alpha-pregnenolone with several hydrazines. Their structures were proved using IR and NMR spectroscopy and mass spectrometry. An x-ray crystal structure analysis was performed for pregnenolone p-nitrophenylhydrazone acetate.
引用
收藏
页码:1024 / 1028
页数:5
相关论文
共 16 条
[1]   Synthesis and antiandrogenic activity of some new 3-substituted androstano[17,16-c]-5′-aryl-pyrazoline and their derivatives [J].
Amr, AEE ;
Abdel-Latif, NA ;
Abdalla, MM .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (02) :373-384
[2]  
[Anonymous], 1996, PROGRAM EMPIRICAL AB
[3]   Studies on novel D-ring substituted steroidal pyrazolines as potential anticancer agents [J].
Banday, Abid H. ;
Mir, Bilal P. ;
Lone, Imtiyaz H. ;
Suri, K. A. ;
Kumar, H. M. Sampath .
STEROIDS, 2010, 75 (12) :805-809
[4]  
CAZAUX JB, 1971, TETRAHEDRON LETT, P41
[5]   Effect of ω-substituents in the hydrazones of conjugated pregnane 20-ketosteroids on their ability to cyclize to pyrazolines [J].
Kamernitskii, A. V. ;
Chernoburova, E. I. ;
Chertkova, V. V. ;
Yarovenko, V. N. ;
Zavarzin, I. V. ;
Krayushkin, M. M. .
RUSSIAN CHEMICAL BULLETIN, 2006, 55 (11) :2117-2118
[6]  
Kamernitskii A V, 2007, Bioorg Khim, V33, P337
[7]  
Kitaev Yu P., 1974, Hydrazones
[8]  
Menshova N. I., 1982, SB NAUCHN T VNIFKHI, V10, p83b
[9]  
Merlani M. I., 2004, Bioorganicheskaya Khimiya, V30, P552
[10]  
Oxford Diffraction, 2009, CRYSALISPRO