(20R)-20-aminopregn-5-en-3β-ol | 5087-58-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (20R)-20-aminopregn-5-en-3β-ol
• 英文别名: 20β-amino-5-pregnen-3β-ol；20β-aminopregn-5-en-3β-ol；(20R)-20-Aminopregn-5-en-3beta-ol；(3S,8S,9S,10R,13S,14S,17S)-17-[(1R)-1-aminoethyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 5087-58-1
• 化学式: C₂₁H₃₅NO
• 分子量: 317.515
• InChiKey: FLEBIYNUTZNISZ-NFJVIFTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (20R)-20-aminopregn-5-en-3β-ol 在 platinum(IV) oxide ammonium hydroxide 、 氢气 、 碘 、 硝酸 、 乙酸酐 、 mercury(II) oxide 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 37.5h， 生成 (20R)-18-iodo-20-nitroamino-5α-pregnan-3β-yl acetate
  参考文献：
  名称：

  Armas, Pedro De; Francisco, Cosme G.; Hernandez, Rosendo, Journal of the Chemical Society. Perkin transactions I, 1988, p. 3255 - 3266

  摘要：

  DOI：
• 作为产物：
  描述：

  20β-aminopregn-5-en-3β-ol 3-THP ether 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 (20R)-20-aminopregn-5-en-3β-ol
  参考文献：
  名称：

  抑制胆固醇侧链裂解。2.差向异构氮杂胆固醇的合成。

  摘要：

  DOI：

  10.1021/jm00282a021

文献信息

• Comparison of anti amoebic activity of stereoisomeric diamino and monoamino pregnene alkaloids and their N-methylated analogs
  作者：RAJ M VAID、K K BHUTANI

  DOI：10.1007/s12039-012-0346-x

  日期：2013.1

  The steroidal alkaloid 3β, 20α-diamino-pregn-5-ene (kurchamine) obtained from the stem bark of Holarrhena antidysenterica is reported to have appreciable amoebicidal activity. Its three stereoisomers namely 3α, 20β-diamino-pregn-5-ene, 3β, 20β-diamino-pregn-5-ene and 3α,20α-diamino-pregn-5-ene and their intermediate stereoisomeric monoamino pregnene alkaloids namely 3β-amino-pregn-5-ene-20-one, 3α-amino-pregn-5-ene-20-one, 20α -amino-pregn-5-ene-3β-ol, 20β-amino-pregn-5-ene-3β-ol were synthesized. The natural stereoisomer and synthesized diamino and monoamino stereoisomers were N-methylated and all the compounds were evaluated for amoebicidal activity comparison. The natural stereoisomer 3β,20α-diamino-pregn-5-ene (kurchamine) was found to be superior than other stereoisomers and N-methylation was found to have insignificant effect on amoebicidal activity of stereoisomers.

  从印度白花木（Holarrhena antidysenterica）的树皮中获得的类固醇生物碱3β, 20α-二氨基孕-5-烯（库尔喹明）据报道具有显著的阿米巴杀灭活性。其三种立体异构体，分别为3α, 20β-二氨基孕-5-烯、3β, 20β-二氨基孕-5-烯和3α, 20α-二氨基孕-5-烯，以及它们的中间立体异构体单氨基孕烯生物碱，包括3β-氨基孕-5-烯-20-酮、3α-氨基孕-5-烯-20-酮、20α-氨基孕-5-烯-3β-醇、20β-氨基孕-5-烯-3β-醇均已合成。天然立体异构体和合成的二氨基及单氨基立体异构体均进行了N-甲基化处理，并对所有化合物的阿米巴杀灭活性进行了比较评估。结果发现，天然立体异构体3β, 20α-二氨基孕-5-烯（库尔喹明）优于其他立体异构体，而N-甲基化对立体异构体的阿米巴杀灭活性影响不显著。
• Discovery and biological evaluation of pregnenolone selenocyanoamides with potential anticancer and antimicrobial activities
  作者：Yanmin Huang、Wenhao Tian、Zining Peng、Yang Cheng、Meizhen Wei、Zhiping Liu、Liping Pang、Jianguo Cui

  DOI：10.1016/j.jsbmb.2023.106388

  日期：2023.11

  that closely related to human hormone expression levels. The Annexin V assay of compound 4f revealed that compounds inhibited tumor cell proliferation primarily through the induction of programmed apoptosis. The zebrafish test results indicated that compound 4d had significant inhibitory activity against MCF-7 cell xenografts in vivo. Moreover, the antibacterial test indicated that compounds 4a and 4d-4e

  从孕烯醇酮开始，通过一系列化学反应将20-羰基转化为氨基。该氨基进一步转化为硒代氰基烷基酰胺，从而合成了六种孕烯醇酮硒代氰基烷基酰胺衍生物。然后对这些化合物进行体外抗肿瘤活性筛选，取得了有希望的结果。化合物4b - 4f对与人类激素表达水平密切相关的乳腺癌、卵巢癌和宫颈癌细胞系表现出比阳性对照阿比特龙和2-甲氧基雌二醇更高的抑制活性，其IC 50值低于10 μmol/L。化合物4f的膜联蛋白 V 测定表明，化合物主要通过诱导程序性细胞凋亡来抑制肿瘤细胞增殖。斑马鱼试验结果表明，化合物4d对体内MCF-7细胞异种移植物具有显着的抑制活性。此外，抗菌试验表明，化合物4a和4d - 4e对耐甲氧西林金黄色葡萄球菌(MRSA)和耐万古霉素肠球菌(VRE)的抑制活性优于阳性对照万古霉素和氨苄西林。这些结果表明这些化合物有望作为新型抗肿瘤剂或抗菌剂进行进一步研究。
• Steroids, LIII: New routes to aminosteroids
  作者：Z. Szendi、G. Dombi、I. Vincze

  DOI：10.1007/bf00844694

  日期：1996.11

  Steroid ketoximes were reduced with sodium tetrahydroborate in the presence of nickel chloride or molybdenum trioxide. These processes yielded 17 alpha- and 20 alpha- aminosteroids (1c-5c) in higher yields than common reduction methods.
• New steroidal nitrosoureas
  作者：Claude Chavis、Chantal de Gourcy、Jean-Louis Borgna、Jean-Louis Imbach

  DOI：10.1016/0039-128x(82)90081-2

  日期：1982.2

  Reformatsky reaction of 3beta, 21-diacyloxy-and 3beta-methoxy-21-acyloxy-5-pregnen-20-one with ethyl bromoacetate yields, through an intramolecular 1,2-acyl migration, 38, 20 XI-diacyloxy- and 3 beta-methoxy-20 XI-acyloxy-14alpha-card-5-enolide respectively. The 20 XI-acyloxy-14, alpha-card-5-enolides were converted into the respective 20 XI-hydroxy-14alpha-card-5-enolides and the 14 alpha card-5,20(22)-dienolides. Experimental support to the proposed intramolecular 1,2-acyl migration is provided by the use of labelled compounds.
• Synthesis of 20-acetamido-3-aza-A-homo-4a-pregnen-4-one
  作者：C. I. Stassinopoulou

  DOI：10.1021/je00039a039

  日期：1985.1