4α-bromo-5α-cholestan-3β-ol | 1173167-16-2

• 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: 4α-bromo-5α-cholestan-3β-ol
• 英文别名: (3S,4S,5R,8S,9S,10R,13R,14S,17R)-4-bromo-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 1173167-16-2
• 化学式: C₂₇H₄₇BrO
• 分子量: 467.574
• InChiKey: AJPFJZIIAPXLQR-ZXQYGXPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4α-Brom-5α-cholestan-3-on 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以66%的产率得到4α-bromo-5α-cholestan-3β-ol
  参考文献：
  名称：

  4α-Bromo-5α-胆甾3β-ol和nor-5α-胆甾3β-ol衍生物—秀丽隐杆线虫的立体选择性合成和激素活性†

  摘要：

  我们描述了立体选择性合成 4α-溴5α-胆甾醇3β-醇，21-nor-5α-胆固醇3β-ol，27-nor-5α-胆固醇3β-ol和21,27-bisnor-5α-胆固醇3β-ol。为了阐明体内的新陈代谢胆固醇，这些化合物已用于秀丽隐杆线虫的饲养实验。我们的初步结果提供了有关新陈代谢的重要见解。胆固醇 在蠕虫中。

  DOI：

  10.1039/b904001c

文献信息

• Novel anti-nematode therapies targetting STRM-1
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP2269630A1

  公开（公告）日：2011-01-05

  The present invention relates to a compound for use as an anti-helminthic agent, said compound being selected from (i) a compound interfering with the transcription or translation of a nucleic acid sequence encoding a polypeptide having a function of introducing a methyl group at a specific position into the sterol nucleus of a sterol which nucleic acid sequence is (a) a nucleic acid sequence encoding a polypeptide comprising or consisting of the amino acid sequence of SEQ ID NO: 1; (b) a nucleic acid sequence comprising or consisting of the sequence of SEQ ID NO: 2; (c) a nucleic acid sequence which encodes a polypeptide which is at least 70% identical to the sequence of SEQ ID NO: 1;(d) the nucleic acid sequence of (b) wherein T is U; (e) a nucleic acid sequence hybridizing to the complementary strand of a nucleic acid molecule of any of (a) to (d); or (f) a nucleic acid sequence being degenerate to the sequence of the nucleic acid molecule of (d) or (e), wherein said compound is an antisense molecule, siRNA, shRNA, miRNA, aptamer, antibody or a ribozyme, and (ii) a compound interfering with the function of the polypeptide encoded by the nucleic acid sequence of (i) said compound being an antibody, enzyme, peptide or a small organic molecule.

  本发明涉及一种用作抗蠕虫剂的化合物，所述化合物选自(i)干扰编码多肽的核酸序列的转录或翻译的化合物，该多肽具有在特定位置将甲基基团引入甾醇核的功能，其核酸序列为(a)编码多肽的核酸序列，该多肽包括或由SEQ ID NO.1的氨基酸序列组成；(b)编码多肽的核酸序列，该多肽包括或由SEQ ID NO.2的氨基酸序列组成；(c)编码多肽的核酸序列，该多肽与SEQ ID NO.3的氨基酸序列至少70％相同：1 的氨基酸序列组成的多肽的核酸序列；(b) 由 SEQ ID NO: 2 的序列组成的核酸序列；(c) 编码与 SEQ ID NO：1；(d) (b)的核酸序列，其中 T 为 U；(e) 与(a)至(d)中任何一项的核酸分子的互补链杂交的核酸序列；或 (f) 与(d)或(e)的核酸分子序列变性的核酸序列，其中所述化合物是反义分子、 siRNA、shRNA、miRNA、aptamer、抗体或核酶，以及 (ii) 干扰由(i)的核酸序列编码的多肽功能的化合物，所述化合物是抗体、酶、肽或小有机分子。
• [EN] NOVEL ANTI-HELMINTHIC THERAPIES<br/>[FR] NOUVELLES THÉRAPIES ANTI-HELMINTHIQUES
  申请人：MAX PLANCK GESELLSCHAFT

  公开号：WO2010146062A2

  公开（公告）日：2010-12-23

  The present invention relates to a compound for use as an anti-helminthic agent, said compound being selected from (i) a compound interfering with the transcription or translation of a nucleic acid sequence encoding a polypeptide having a function of introducing a methyl group at a specific position into the sterol nucleus of a sterol which nucleic acid sequence is (a) a nucleic acid sequence encoding a polypeptide comprising or consisting of the amino acid sequence of SEQ ID NO: 1; (b) a nucleic acid sequence comprising or consisting of the sequence of SEQ ID NO: 2; (c) a nucleic acid sequence which encodes a polypeptide which is at least 70% identical to the sequence of SEQ ID NO: 1;(d) the nucleic acid sequence of (b) wherein T is U; (e) a nucleic acid sequence hybridizing to the complementary strand of a nucleic acid molecule of any of (a) to (d); or (f) a nucleic acid sequence being degenerate to the sequence of the nucleic acid molecule of (d) or (e), wherein said compound is an antisense molecule, siRNA, shRNA, miRNA, aptamer, antibody or a ribozyme, and (ii) a compound interfering with the function of the polypeptide encoded by the nucleic acid sequence of (i) said compound being an antibody, enzyme, peptide or a small organic molecule.
• 4α-Bromo-5α-cholestan-3β-ol and nor-5α-cholestan-3β-ol derivatives—stereoselective synthesis and hormonal activity in Caenorhabditis elegans
  作者：René Martin、Ratni Saini、Ingmar Bauer、Margit Gruner、Olga Kataeva、Vyacheslav Zagoriy、Eugeni V. Entchev、Teymuras V. Kurzchalia、Hans-Joachim Knölker

  DOI：10.1039/b904001c

  日期：——

  describe the stereoselective synthesis of 4α-bromo-5α-cholestan-3β-ol, 21-nor-5α-cholestan-3β-ol, 27-nor-5α-cholestan-3β-ol and 21,27-bisnor-5α-cholestan-3β-ol. In order to clarify the in vivometabolism of cholesterol, these compounds have been used for feeding experiments in Caenorhabditis elegans. Our preliminary results provide important insights into the metabolism of cholesterol in worms.

  我们描述了立体选择性合成 4α-溴5α-胆甾醇3β-醇，21-nor-5α-胆固醇3β-ol，27-nor-5α-胆固醇3β-ol和21,27-bisnor-5α-胆固醇3β-ol。为了阐明体内的新陈代谢胆固醇，这些化合物已用于秀丽隐杆线虫的饲养实验。我们的初步结果提供了有关新陈代谢的重要见解。胆固醇 在蠕虫中。