活性维生素D_3类药物的研究进展
作者:文鹏;赵梨;吴坚;陆群;
Author:
收稿日期: 年卷(期)页码:2011,26(01):-87-90
期刊名称:华西药学杂志
Journal Name:WEST CHINA JOURNAL OF PHARMACEUTICAL SCIENCES
关键字:活性维生素D3;结构修饰;类似物;构效关系
Key words:
基金项目:四川省科技计划资助项目(2010SZ0124);;
中央高校基本科研业务费专项资金资助项目(SWJTU2010ZT09;SWJTU09CX062)
中文摘要
通过对活性维生素D3化学结构进行修饰,获得了大量高效低毒的抗癌活性类似物。综述了活性维生素D3的A环结构修饰方法及其类似物的构效关系。
参考文献
[1]AbeE,MiyauraC,Sakagami H,et al.Differentiationof mousemye-loid leukemia cells induced by 1 alpha,25-dihydroxyvitamin D3[J].Proc Natl Acad Sci USA,1981,78(8):4990-4994.
[2]Brown A,Slatopolsky E.Vitamin d analogs:therapeutic applica-tions and mechanisms for selectivity[J].Mol Aspects Med,2008,29(6):433-452.
[3]Okano T,Tsugawa N,Masuda S,et al.Regulatory activities of2 be-ta-(3-hydroxypropoxy)-1 alpha,25-dihydroxyvitamin D3,anovel synthetic vitamin D3 derivative,on calcium metabolism[J].Biochem Biophys Res Commun,1989,163(3):1444-1449.
[4]Perlman K,Sicinski R,Schnoes H,et al.1[alpha],25-dihydroxy-19-nor-vitamin D3,a novel vitamin d-relatedcompound with potential therapeutic activity[J].TetrahedronLett,1990,31(13):1823-1824.
[5]俞银芳,刘兆鹏.活性维生素D3类药物研究概况[J].中国药物化学杂志,2006,16(5):311-315.
[6]Norman A,BishopJ,CollinsE,et al.Differingshapesof1α,25-dihydroxyvitamin D3 function as ligands for the d-binding pro-tein,nuclear receptor and membrane receptor:A status report[J].JSteroid Biochem,1996,56(1-6):13-22.
[7]Ohshima E,Sai H,Takatsuto S,et al.Synthesis and biological ac-tivity of 1α-fluoro-25-hydroxyvitamin D3[J].Chem PharmBull,1984,32(9):3525-3531.
[8]Oves D,Fernandez S,Ferrero M,et al.Versatile synthesis and bio-logical evaluation of 1,3-diamino-substituted 1α,25-di-hydroxyvitamin D3 analogues[J].Bioorgan Med Chem,2006,14(4):928-937.
[9]Posner G,Suh B,Petersen K,et al.Difluoromethyl analogs of thenatural hormone 1[alpha],25-dihydroxyvitamin D3:Design,syn-thesis,and preliminary biological evaluation[J].J Steroid Bio-chem,2007,103(3-5):213-221.
[10]Posner G,Nelson T,Guyton K,et al.New vitamin D3 derivativeswith unexpected antiproliferative activity:1-(hydroxymethyl)-25-hydroxyvitamin D3 homologs[J].J Med Chem,1992,35(17):3280-3287.
[11]Norman A,Bouillon R,Farach-Carson M,et al.Demonstrationthat 1 beta,25-dihydroxyvitamin D3 is an antagonist of the non-genomic but not genomic biological responses and biological profileof the three a-ring diastereomers of 1 alpha,25-dihydroxyvitaminD3[J].J Biol Chem,1993,268(27):20022.
[12]Nishii Y,OkanoT.Historyof thedevelopment of new vitamind an-alogs:Studies on 22-oxacalcitriol(oct)and 2α-(3-hydroxypropoxy)calcitriol(ed-71)[J].Steroids,2001,66(3-5):137-146.
[13]Fujishima T,Zhaopeng L,Konno K,et al.Highly potent cell differ-entiation-inducing analogues of 1α,25-dihydroxyvitamin D3:Synthesis and biological activity of 2-methyl-1,25-di-hydroxyvitamin D3 with side-chain modifications[J].Bioorg MedChem,2001,9(2):525-535.
[14]Honzawa S,SuharaY,Nihei K,et al.Concisesynthesisandbiologi-cal activities of 2α-alkyl-and 2α-(w-hydroxyalkyl)-20-epi-1α,25-dihydroxyvitamin D3[J].Bioorg Med Chem Lett,2003,13(20):3503-3506.
[15]Saito N,Suhara Y,Abe D,et al.Synthesis of 2α-propoxy-1α,25-dihydroxyvitamin D3 and comparison of its metabolism by hu-man cyp24a1 and rat cyp24a1[J].Bioorg Med Chem,2009,17(13):4296-4301.
[16]Fujishima T,Kittaka A,Kurihara M,et al.2,2-functionalizedanalogues of 1α,25-dihydroxyvitamin D3,the potent inducers ofcell differentiation[J].J Steroid Biochem Mol Biol,2004,89:89-92.
[17]Honzawa S,Hirasaka K,Yamamoto Y,et al.Design,synthesis andbiological evaluation of novel 1α,25-dihydroxyvitamin D3 ana-logues possessing aromatic ring on 2α-position[J].Tetrahedron,2005,61(47):11253-11263.
[18]Messerlian S,Gao X,St-Arnaud R.The 3-epi-and 24-oxo-derivatives of 1α,25 dihydroxyvitamin D3 stimulate transcriptionthrough the vitamin d receptor[J].J Steroid Biochem Mol Biol,2000,72(1-2):29-34.
[19]Gotor-FernandezV,FernandezS,FerreroM,etal.Chemoenzymat-ic synthesis and biological evaluation of c-3 carbamate analoguesof 1α,25-dihydroxyvitamin D3[J].Bioorg Med Chem,2004,12(20):5443-5451.
[20]Bouillon R,Sarandeses L,Allewaert K,et al.Biologic activity of di-hydroxylated 19-nor-(pre)vitamin D3[J].J Bone Miner Res,1993,8(8):1009-1015.
[21]Chen T,Persons K,Zheng S,et al.Evaluation of c-2-substituted19-nor-1[alpha],25-dihydroxyvitamin D3 analogs as thera-peutic agents for prostate cancer[J].J Steroid Biochem Mol Biol,2007,103(3-5):717-720.
[22]Sicinski R,Perlman K,DeLuca H.Synthesis and biological activityof 2-hydroxy and 2-alkoxy analogs of 1α,25-dihydroxy-19-norvitamin d3[J].J Med Chem,1994,37(22):3730-3738.
[23]OkanoT,NakagawaK,KuboderaN,etal.Catalyticasymmetricsyn-theses and biological activities of singly dehydroxylated 19-nor-1α,25-dihydroxyvitamin D3 a-ring analogs in cancer cell differ-entiation and apoptosis[J].Chem Biol,2000,7(3):173-184.
[24]Sicinski R,RotkiewiczP,Kolinski A,et al.2-ethyl and2-ethyli-dene analogues of 1[alpha],25-dihydroxy-19-norvitamin D3:Synthesis,conformational analysis,biological activities,and doc-king to the modeled rvdr ligand binding domain[J].J Med Chem,2002,45(16):3366-3380.
[25]Shimizu M,Miyamoto Y,Kobayashi E,et al.Synthesis and biolog-ical activities of new 1α,25-dihydroxy-19-norvitamin D3 ana-logs with modifications in both the a-ring and the side chain[J].Bioorg Med Chem,2006,14(12):4277-4294.
[26]Kobayashi E,Shimazaki M,Miyamoto Y,et al.Structure-activityrelationships of 19-norvitamin d analogs having a fluoroethylidenegroup at the c-2 position[J].Bioorg Med Chem,2007,15(3):1475-1482.
[27]Shimazaki M,Miyamoto Y,Yamamoto K,et al.Analogs of1α,25-dihydroxyvitamin D3 with high potency in induction of osteoclasto-genesis and prevention of dendritic cell differentiation:Synthesisand biological evaluation of 2-substituted 19-norvitamin d ana-logs[J].Bioorg Med Chem,2006,14(13):4645-4656.
[28]Glebocka A,Sicinski R,DeLuca H.New derivative of 1α,25-di-hydroxy-19-norvitamin D3 with 3'-alkoxypropylidene moiety atc-2:Synthesis,biological activity and conformational analysis[J].J Steroid Biochem Mol Biol,2004,89:25-30.
[29]Kanzler S,Halkes S,van de Velde J,et al.A novel class of vitaminD analogs synthesis and preliminary biological evaluation[J].Bioorg Med Chem Lett,1996,6(15):1865-1868.
[30]Fujishima T,Konno K,Nakagawa K,et al.Synthesis and biologicalevaluation of all a-ring stereoisomers of 5,6-trans-2-methyl-1,25-dihydroxyvitamin D3 and their 20-epimers:Possi-ble binding modes of potent a-ring analogues to vitamin D recep-tor[J].Chem Biol,2001,8(11):1011-1024.
[31]Suhara Y,Kittaka A,Ono K,et al.Design and efficient synthesis ofnew stable 1α,25-dihydroxy-19-norvitamin D3 analogues con-taining amide bond[J].Bioorg Med Chem Lett,2002,12(24):3533-3536.
[32]Posner G,Lee S,Kim H,et al.Novel a-ring analogs of the hor-mone 1α,25-dihydroxyvitamin D3:Synthesis and preliminary bio-logical evaluation[J].Bioorg Med Chem,2005,13(8):2959-2966.
【关闭】