3β-hydroxy-22-piperidino-23,24-bisnor-chol-5-ene | 31056-33-4

• 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: 3β-hydroxy-22-piperidino-23,24-bisnor-chol-5-ene
• 英文别名: 22-piperidino-23,24-dinor-chol-5-en-3β-ol；(20S)-20-[(piperidin-1-yl)methyl]-5α-pregna-5-en-3β-ol；(3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-[(2S)-1-piperidin-1-ylpropan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 31056-33-4
• 化学式: C₂₇H₄₅NO
• 分子量: 399.66
• InChiKey: XVTNSCZZDCNOFK-DPAQBDIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3β-acetoxybisnor-5-cholenic acid 在 吡啶 、 lithium hydroxide 、 dimethyl sulfide borane 、 四丁基碘化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 3β-hydroxy-22-piperidino-23,24-bisnor-chol-5-ene
  参考文献：
  名称：

  Preparation of transition-state analogues of sterol 24-methyl transferase as potential anti-parasitics

  摘要：

  There is an urgent need for new drugs to treat leishmaniasis and Chagas disease. One important drug target in these organisms is sterol biosynthesis. In these organisms the main endogenous sterols are ergosta- and stigmata-like compounds in contrast to the situation in mammals, which have cholesterol as the sole sterol. In this paper we discuss the design, synthesis and evaluation of potential transition state analogues of the enzyme Delta(24(25))-methyltransferase (24-SMT). This enzyme is essential for the biosynthesis of ergosterol, but not required for the biosynthesis of cholesterol. A series of compounds were successfully synthesised in which mimics of the S-adenosyl methionine co-factor were attached to the sterol nucleus. Compounds were evaluated against recombinant Leishmania major 24-SMT and the parasites L. donovani and Trypanosoma cruzi in vitro, causative organisms of leishmaniasis and Chagas disease, respectively. Some of the-compounds showed inhibition of the recombinant Leishmania major 24-SMT and induced growth inhibition of the parasites. Some compounds also showed anti-parasitic activity against L. donovani and T cruzi, but no inhibition of the enzyme. In addition, some of the compounds had anti-proliferative activity against the bloodstream forms of Trypanosoma brucei rhodesiense, which causes African trypanosomiasis. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2005.06.012

文献信息

• Steroid compounds, use of these compounds for the preparation of meiosis-regulating medicaments and method for the preparation of these compounds
  申请人：Schering AG

  公开号：US20020188143A1

  公开（公告）日：2002-12-12

  The present invention relates to steroid compounds of general formula X, which may advantageously be employed to stimulate meiosis in human oocytes, the steroid being specifically characterized by amino nitrogen bonded to C 17 of the steroid skeleton via a spacer A. 1

  本发明涉及通式X的类固醇化合物，这些化合物可优势地用于刺激人卵母细胞的减数分裂，该类固醇化合物的特征在于氨基氮通过间距A.1与类固醇骨架的C17键合。
• Steroid Amines. Fungicides Derived from Δ⁵-3β-Hydroxybisnorcholenic Acid (Fernholz Acid)
  作者：Hershel L. Herzog、Constance C. Payne、E. B. Hershberg

  DOI：10.1021/ja01625a036

  日期：1955.10
• US6916921B2
  申请人：——

  公开号：US6916921B2

  公开（公告）日：2005-07-12
• [EN] USE OF MAS-COMPOUNDS FOR TREATING DISEASES ASSOCIATED WITH LIPID METABOLISM<br/>[FR] UTILISATION DE COMPOSES MAS POUR LE TRAITEMENT DES MALADIES ASSOCIEES AU METABOLISME DES LIPIDES
  申请人：NOVO NORDISK AS

  公开号：WO2004028544A1

  公开（公告）日：2004-04-08

  Certain sterols can be used for increasing the HDL cholesterol to non-HDL cholesterol ratio, for treatment and/or prevention of artherosclerosis, for treatment and/or prevention of hyper-lipidemia, for treatment of diabetic dyslipididemia, for treatment of hyper-cholesterolemia, for treatment of diseases of illness related to metabolic dysfunction, for treatment of obesity or obesitas related diseases, and for the treatment of neurological diseases.