(3β)-3-(acetyloxy)chol-5-en-24-oyl chloride | 51658-29-8

• 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)-3-(acetyloxy)chol-5-en-24-oyl chloride
• 英文别名: 3β-acetoxy-5-cholenic acid chloride；3β-acetoxychol-5-en-24-oyl chloride；3β-acetoxy-5-cholenyl chloride；3β-acetoxy-cholen-(5)-oic acid-(24)-chloride；3β-Acetoxy-cholen-(5)-saeure-(24)-chlorid；3β-Acetoxy-cholen-(5)-oxy-(24)-chlorid；3beta-Acetoxy-delta5-cholenyl Chloride；[(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-5-chloro-5-oxopentan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 51658-29-8
• 化学式: C₂₆H₃₉ClO₃
• 分子量: 435.047
• InChiKey: QIBNDKKFQYRWDS-WBNKZLQISA-N

物化性质

• 沸点：
  502.3±33.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3β)-3-(acetyloxy)chol-5-en-24-oyl chloride 在 diisobutylcadmium 作用下， 以 苯 为溶剂， 反应 20.0h， 生成 24-oxo-24-homocholesteryl acetate
  参考文献：
  名称：

  Minor and trace sterols in marine invertebrates. 31. Isolation and structure elucidation of 23H-isocalysterol, a naturally occurring cyclopropene. Some comparative observations on the course of hydrogenolytic ring opening of steroidal cyclopropenes and cyclopropanes

  摘要：

  DOI：

  10.1021/ja00388a041
• 作为产物：
  描述：

  3β-acetoxy-5-cholenic acid 在 草酰氯 作用下， 以 苯 为溶剂， 生成 (3β)-3-(acetyloxy)chol-5-en-24-oyl chloride
  参考文献：
  名称：

  Preparation of cholesterol-25-3H

  摘要：

  这里介绍的胆固醇-25-3H（9）的合成是从现成的 3β-hydroxy-δ5-cholenic acid（1）开始的。通过 Arndt-Eistert 方法将这种酸的乙酸酯转化为下一级同系物。与碘甲烷进行格氏反应后得到 25-羟基胆固醇（6），然后对其进行溴化处理。最后用 LiAl3H4 处理 25-溴胆固醇 (8)，引入氚。

  DOI：

  10.1002/jlcr.2590050112

文献信息

• Steroid derivatives, pharmaceutical compositions containing them, and
  申请人：Magainin Pharmaceuticals, Inc.

  公开号：US05637691A1

  公开（公告）日：1997-06-10

  Compounds having a broad range of antimicrobial activity generally have a structure including asteroid nucleus with a cationic, preferably polyamine, side chain (X) and an anionic side chain (Y). The invention is also directed to compounds of the Formula III: ##STR1## preferably where the steroid ring nucleus is saturated; the steroid ring substituent Z.sub.5 is .alpha.-H; one Z.sub.7 is .beta.-H and the other is .alpha.-H or .alpha.-OH; both substituents Z.sub.12 are hydrogen; X' is a polyamine side chain of the formula --NH--(CH.sub.2).sub.p --NH--(CH.sub.2).sub.q --N(R.sup.II)(R.sup.III) where p and q are each independently 3 or 4, and R.sup.II and R.sup.III are each independently hydrogen or methyl; R' is methyl; and Y' is (C.sub.1 -C.sub.10)-alkyl substituted with a group such as --CO.sub.2 H or --SO.sub.3 H.

  具有广泛抗微生物活性的化合物通常具有包括阳离子侧链（X）和阴离子侧链（Y）的类固醇核心的结构。该发明还涉及以下式III的化合物：##STR1## 最好是类固醇环核饱和；类固醇环取代基Z.sub.5为α-H；一个Z.sub.7为β-H，另一个为α-H或α-OH；两个取代基Z.sub.12为氢；X'是具有式--NH--(CH.sub.2).sub.p --NH--(CH.sub.2).sub.q --N(R.sup.II)(R.sup.III)的多胺侧链，其中p和q各自独立地为3或4，R.sup.II和R.sup.III各自独立地为氢或甲基；R'为甲基；Y'为（C.sub.1 -C.sub.10）烷基，取代有--CO.sub.2 H或--SO.sub.3 H等基团。
• Method for inhibiting angiogenesis using squalamine and squalamine
  申请人：Magainin Pharmaceuticals Inc.

  公开号：US05721226A1

  公开（公告）日：1998-02-24

  A method of inhibiting angiogenesis in a patient includes administering to the patient an effective amount of squalamine or a pharmaceutically acceptable salt of squalamine. Alternatively, a compound according to the following Formula (III) (or a pharmaceutically acceptable salt thereof) can be administered: ##STR1## wherein Z.sub.5 is .alpha.-H or .beta.-H; each of the substituents Z.sub.7 is selected from the group of --H, --OH, --SH, --NH.sub.2, --F, --(C.sub.1 -C.sub.3)-alkyl, and --(C.sub.1 -C.sub.3)-alkoxy; and one of the substituents Z.sub.12 is --H and the other is --H or --OH. X' is a polyamine side chain of the formula --X.sub.1 --(CH.sub.2).sub.p --X.sub.2 --(CH.sub.2).sub.q --N(R.sup.II)(R.sup.III), wherein one of X.sub.1 and X.sub.2 is --N(R.sup.IV) and the other is selected from the group of --N(R.sup.V), --O, --S, and --CH.sub.2. R.sup.IV and R.sup.V are each --H or --(C.sub.1 -C.sub.3)-alkyl, p and q are each an integer of from 0 to 5 (but both are not 0). R.sup.II and R.sup.III in the formula for X' are each --H, --(C.sub.1 -C.sub.3)-alkyl, or --(CH.sub.2).sub.r --N(R.sub.10)(R.sub.11) wherein r is an integer from 2 to 5 and R.sub.10 and R.sub.11 are each --H or --(C.sub.1 -C.sub.3)-alkyl. R' in Formula (III) is --H or --(C.sub.1 -C.sub.3)-alkyl, and Y' is --(C.sub.1 -C.sub.10)-alkyl, unsubstituted or substituted with --CO.sub.2 H, --OH, --NH--SO.sub.2 CF.sub.3, --SO.sub.3 H, --PO.sub.3 H.sub.2, --OSO.sub.3 H, --CF.sub.3, --F, ##STR2##

  在患者中抑制血管生成的方法包括向患者施用一定量的鲨烷或鲨烷的药用盐。或者，可以施用以下式（III）所示的化合物（或其药用盐）：##STR1## 其中Z.sub.5为α-H或β-H；Z.sub.7的取代基选自--H、--OH、--SH、--NH.sub.2、--F、--（C.sub.1 -C.sub.3）-烷基和--（C.sub.1 -C.sub.3）-氧烷基的群；其中一个取代基Z.sub.12为--H，另一个为--H或--OH。X'为具有以下式--X.sub.1 --（CH.sub.2）.sub.p --X.sub.2 --（CH.sub.2）.sub.q --N（R.sup.II）（R.sup.III）的多胺侧链，其中X.sub.1和X.sub.2中的一个为--N（R.sup.IV），另一个选自--N（R.sup.V）、--O、--S和--CH.sub.2的群。R.sup.IV和R.sup.V分别为--H或--（C.sub.1 -C.sub.3）-烷基，p和q分别为0到5的整数（但两者都不为0）。X'中的公式中的R.sup.II和R.sup.III分别为--H、--（C.sub.1 -C.sub.3）-烷基或--（CH.sub.2）.sub.r --N（R.sub.10）（R.sub.11），其中r为2到5的整数，R.sub.10和R.sub.11分别为--H或--（C.sub.1 -C.sub.3）-烷基。式（III）中的R'为--H或--（C.sub.1 -C.sub.3）-烷基，Y'为--（C.sub.1 -C.sub.10）-烷基，未取代或取代为--CO.sub.2 H、--OH、--NH--SO.sub.2 CF.sub.3、--SO.sub.3 H、--PO.sub.3 H.sub.2、--OSO.sub.3 H、--CF.sub.3、--F、##STR2##
• FREE CHOLESTEROL ANALOGS BEARING A BORON DIPYRROMETHENE DIFLUORO (BODIPY) FLUOROPHORE IN THE SIDE CHAIN AND METHOD OF PREPARATION AND USE THEREOF
  申请人：Bittman Robert

  公开号：US20080177059A1

  公开（公告）日：2008-07-24

  The present invention relates to free cholesterol analogs bearing a boron dipyrromethene difluoro (BODIPY) fluorophore in the side chain and methods of preparation. The compounds of the present invention can be used in fluorescence spectroscopy and fluorescence microscopy to visualize the exchange, distribution, and trafficking of free cholesterol between living cells and to monitor the movement of free cholesterol between ordered and disordered lipid domains in membranes.

  本发明涉及带有硼二吡咯甲烷二氟（BODIPY）荧光团的游离胆固醇类似物及其制备方法。本发明的化合物可用于荧光光谱学和荧光显微镜技术，以可视化活细胞之间游离胆固醇的交换、分布和转运，并监测游离胆固醇在膜中有序和无序脂质域之间的运动。
• Synthesis of squalamine. A steroidal antibiotic from the shark
  作者：Robert M. Moriarty、Sudersan M. Tuladhar、Liang Guo、Suzanne Wehrli

  DOI：10.1016/0040-4039(94)88254-1

  日期：1994.10

  The title compound was synthesized from 3β-acetoxy-5-cholenic acid () in 17 steps.

  由17个步骤由3β-乙酰氧基-5-胆酸（）合成标题化合物。
• Method for treating infection using steroid based pharmaceutical
  申请人：Magainin Pharmaceuticals Inc.

  公开号：US05733899A1

  公开（公告）日：1998-03-31

  A method of treating a bacterial or fungal infection in a patient by administering an effective amount of a compound of Formula (III): ##STR1## wherein, the substituents are as defined in the specification.

  通过给患者注射有效量的公式（III）化合物，治疗细菌或真菌感染的方法：##STR1## 其中，取代基如规范中所定义。