3β-acetoxy-cholest-5-en-24-one | 20981-59-3

• 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-acetoxy-cholest-5-en-24-one
• 英文别名: 24-keto-cholesteryl acetate；3β-acetoxycholestan-5-en-24-one；Δ⁵-3β-hydroxycholestene-24-one-3-acetate；3-acetoxyl-5-en-cholest-24-one；oxocholesterol acetate；(3β)-3-(acetyloxy)-cholest-5-en-24-one；3β-hydroxycholest-5-en-24-one acetate；3β-acetoxy-24-oxo-5-cholestene；3β-acetoxy-24-oxocholest-5-ene；3β-Acetoxy-cholest-5-en-24-on；3β-hydroxycholest-5-en-24-on acetate；24-oxocholesterol acetate；[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methyl-5-oxoheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 20981-59-3
• 化学式: C₂₉H₄₆O₃
• 分子量: 442.682
• InChiKey: XLVMMFHWIROLGG-HSIBUNQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 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-acetoxy-cholest-5-en-24-one 在 氢氧化钾 、 sodium hydride 作用下， 以 1,4-二氧六环 、 吡啶 、 甲醇 、 二甲基亚砜 为溶剂， 反应 26.25h， 生成 24-methylene cholesteryl acetate
  参考文献：
  名称：

  Synthesis of polyhydroxysterols (V): efficient and stereospecific synthesis of 24-methylene-cholest-5-ene-3β,7α-diol and its C-7 epimer

  摘要：

  This paper describes the efficient and stereospecific synthesis of cytotoxicdihydroxylated sterols, 24-methylene-cholest-5-ene-3beta,7alpha-diol 1, and its C-7 epimer, 24-methylene-cholest-5-ene-3beta,7beta-diol 2. The crux of the synthesis is that the selective allylic oxidation of 24-methylenecholesteryl acetate proceeds to 24-niethylene-7-keto-cholesteryl acetate without extensive by product formation from reaction at the Delta24(28) double bond. This methodology may be useful for the preparation of other oxysterols with non-standard side chains. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.09.010
• 作为产物：
  描述：

  胆固醇 在 N-羟基丁二酰亚胺 、 iron naphthenate 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 3β-acetoxy-cholest-5-en-24-one
  参考文献：
  名称：

  一种制备环状α,β-不饱和酮的方法

  摘要：

  本发明提供了一种制备环状α,β‑不饱和酮的方法。所述方法是式(I)所示化合物在催化剂及助剂存在下，通过电化学合成被氧气氧化，制备式(II)所示化合物：所述方法条件温和，原子经济性高，三废少，产品收率高＞95％。

  公开号：

  CN111302925B

文献信息

• Stereochemical fate of the isopropylidene methyl groups of lanosterol during the biosynthesis of isofucosterol in Pinus pinea
  作者：Francesco Nicotra、Fiamma Ronchetti、Giovanni Russo、Giuseppe Lugaro、Marilena Casellato

  DOI：10.1039/p19810000498

  日期：——

  [26-3H]Lanosterol (16) was administered to Pinus pinea and the [26-3H]isofucosteryl acetate (6) obtained was chemically transformed into [26-3H]cholesterol (13). Compound (13) was incubated with rat-liver mitochondria to yield [3-3H] propionic acid. The data obtained are consistent with a biosynthetic pathway in which the pro-E isopropylidene methyl group of the Δ24-precursor becomes the pro-R isopropyl

  [26- 3 H]羊毛甾醇（16）中的溶液施用至松pinea和[26- 3 H]乙酸isofucosteryl（6）中得到的化学转化成[26- 3 H]胆固醇（13）。将化合物（13）与大鼠肝线粒体一起温育以产生[3- 3 H]丙酸。获得的数据是具有生物合成途径相一致，其中所述亲的Δ的-E异亚甲基24 -precursor变为亲-R异丙基甲基组中isofucosterol。
• 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##
• Synthesis and bioactivities of steroid derivatives as antifungal agents
  作者：Sung-Kee Chung、Chung Hwan Ryoo、Hong Woon Yang、Jeung-Yeop Shim、Myung Goo Kang、Ki Wha Lee、Heui Il Kang

  DOI：10.1016/s0040-4020(98)01000-x

  日期：1998.12

  A series of lanosterol and cholesterol derivatives with modified side chain structures, which might interfere with sterol C24-methyltransferase in the ergosterol biosynthesis as substrate analogs, have been synthesized. The in vitro bioassay studies have shown that some of these compounds, in particular with C24-amino- and thio-functionalities, possess potent antifungal activities, in vivo. Bioassays

  已经合成了一系列具有修饰的侧链结构的羊毛甾醇和胆固醇衍生物，其可能作为底物类似物干扰麦角固醇生物合成中的固醇C24-甲基转移酶。在体外生物测定研究已经表明，这些化合物的一些，特别是C24-氨基和硫代官能团时，具有有效的抗真菌活性，在体内。还对主要化合物进行了生物测定。
• A highly stereoselective synthesis of C-24 and C-25 oxysterols from desmosterol
  作者：Qian Zhao、Chao Qian、Xin-Zhi Chen

  DOI：10.1016/j.steroids.2016.03.003

  日期：2016.5

  A new highly stereoselective construction of the side chain of the C-24 and C-25 oxysterols has been achieved by using desmosterol acetate as the starting material and an improved Sharpless catalytic asymmetric dihydroxylation with 100% d.e. (diastereomeric excess) as the key step. The result is much better than the usual asymmetric dihydroxylation procedure. t-Butyl nitrite/2,2,6,6-tetramethylpiperidine

  C-24和C-25氧固醇的侧链具有高度立体选择性的新结构，这是通过使用醋酸去甾醇作为起始原料，并以100％的de（非对映异构体过量）作为主要步骤，改进了Sharpless催化不对称二羟基化反应而实现的。结果比通常的不对称二羟基化方法好得多。开发了亚硝酸叔丁酯/ 2,2,6,6-四甲基哌啶N-氧基自由基/ FeCl3催化剂体系，以活化分子氧以进行24-羟基胆固醇的好氧氧化，并以86.2％的收率获得了24-酮胆固醇。以前从未报道过氧化系统。还提出了催化好氧氧化的机理。