5,24(28)-胆甾二烯-24-亚甲基-3beta-醇 | 474-63-5

• 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
• 中文名称: 5,24(28)-胆甾二烯-24-亚甲基-3beta-醇
• 中文别名: 海绵甾醇；24-亚甲基胆固醇牡蛎甾醇
• 英文名称: 24-methylene cholesterol
• 英文别名: 24-Methylenecholesterol；(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 474-63-5
• 化学式: C₂₈H₄₆O
• 分子量: 398.673
• InChiKey: INDVLXYUCBVVKW-PXBBAZSNSA-N

物化性质

• 溶解度：
  氯仿（微溶）、甲醇（微溶、加热）
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• WGK Germany：
  3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  链甾醇	demosterol	313-04-2	C27H44O	384.646
  豆甾醇	Stigmasterol	83-48-7	C29H48O	412.7
  (3beta,20S)-20-甲酰基-3-羟基-5-孕烯	cholest-5-en-3β-ol-22-al	53906-49-3	C22H34O2	330.511
  ——	24-oxocholesterol	17752-16-8	C27H44O2	400.645
  ——	(22-trans)-3β-hydroxy-cholest-5,22-diene-24-one	89495-47-6	C27H42O2	398.629
  ——	3β-acetoxy-cholest-5-en-24-one	20981-59-3	C29H46O3	442.682

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  胆固醇	cholesterol	57-88-5	C27H46O	386.662
  链甾醇	demosterol	313-04-2	C27H44O	384.646
  岩皂甾醇	28-Isofucosterol	17605-67-3	C29H48O	412.7
  ——	isofucosterol	481-14-1	C29H48O	412.7
  桐甾醇	clerosterol	2364-23-0	C29H48O	412.7
  ——	25-dehydroaplysterol	70284-75-2	C29H48O	412.7
  ——	ergosta-5,23(Z)-dien-3β-ol	82949-88-0	C28H46O	398.673
  ——	24-methyl-23-dehydrocholesterol	79733-00-9	C28H46O	398.673
  ——	epicodisterol	71486-08-3	C28H46O	398.673
  ——	codisterol	52936-69-3	C28H46O	398.673

反应信息

• 作为反应物：
  描述：

  5,24(28)-胆甾二烯-24-亚甲基-3beta-醇 以17.9%的产率得到胆固醇
  参考文献：
  名称：

  Biosynthesis of marine lipids. 19. Dealkylation of the sterol side chain in sponges

  摘要：

  DOI：

  10.1021/ja00228a055
• 作为产物：
  描述：

  豆甾醇 在 platinum(IV) oxide 盐酸 、 iodobenzene dibromide 、 氢气 、 sodium hydride 、 potassium carbonate 、 臭氧 、 formamide 、 二甲基亚砜 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 37.5h， 生成 5,24(28)-胆甾二烯-24-亚甲基-3beta-醇
  参考文献：
  名称：

  Synthesis of polyhydroxysterols (III): synthesis and structural elucidation of 24-methylenecholest-4-en-3β,6α-diol

  摘要：

  Using stigmasterol as the starting material, 24-methylenecholest-4-en-3beta,6alpha-diol (2) was synthesized in eight steps in 13% overall yield. The introduction of the sterol side-chain was carried out using (3-methyl-2-oxobutyl)-triphenylarsonium bromide (11) and K2CO3 in a solid-liquid phase-transfer Wittig reaction. Construction of the steroidal nucleus was finished by oxidation of 24-methylenecholest-5-en-3beta-ol (9) with pyridinium chlorochromate (PCC) in dichloromethane at ambient temperature and by reduction of 24-methylenecholest-4-en-3,6-dione (10) with NaBH4 in the presence of CeCl3.7H(2)O. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00059-4

文献信息

• An Enzyme-Based Formaldehyde Assay and Its Utility in a Sponge Sterol Biosynthetic Pathway
  作者：Russell G. Kerr、Kathleen Kelly

  DOI：10.1021/np980366d

  日期：1999.1.1

  An enzyme-based assay has been developed and utilized to confirm the production of formaldehyde in the dealkylation of sterol side chains in a marine sponge. The enzyme used in the assay, formaldehyde dehydrogenase, is NAD+ dependent, and the assay measures the production of NADH by determining the increase in fluorescence at 460 nm.

  已经开发了一种基于酶的测定法，并用于确认海洋海绵中固醇侧链脱烷基化过程中甲醛的产生。分析中使用的酶甲醛脱氢酶是NAD +依赖性的，该分析通过确定460 nm处荧光的增加来测量NADH的产生。
• Marine and Semi-Synthetic Hydroxysteroids as New Scaffolds for Pregnane X Receptor Modulation
  作者：Valentina Sepe、Francesco Di Leva、Claudio D'Amore、Carmen Festa、Simona De Marino、Barbara Renga、Maria D'Auria、Ettore Novellino、Vittorio Limongelli、Lisette D'Souza、Mahesh Majik、Angela Zampella、Stefano Fiorucci

  DOI：10.3390/md12063091

  日期：——

  In recent years many sterols with unusual structures and promising biological profiles have been identified from marine sources. Here we report the isolation of a series of 24-alkylated-hydroxysteroids from the soft coral Sinularia kavarattiensis, acting as pregnane X receptor (PXR) modulators. Starting from this scaffold a number of derivatives were prepared and evaluated for their ability to activate

  近年来，已从海洋来源中鉴定出许多具有不寻常结构和有希望的生物特征的甾醇。在这里，我们报告了从软珊瑚 Sinularia kavarattiensis 中分离出一系列 24-烷基化羟基类固醇，作为孕烷 X 受体 (PXR) 调节剂。从该支架开始，制备了许多衍生物，并通过评估反式激活和量化基因表达来评估它们激活 PXR 的能力。我们的研究表明，ergost-5-en-3β-ol (4) 在 HepG2 细胞中诱导 PXR 反式激活并刺激 PXR 靶基因 CYP3A4 的表达。为了阐明这些配体与 PXR 之间相互作用的分子基础，我们通过对接模拟研究了该系列中最有效的化合物 4 与 PXR 的结合机制。
• [EN] LIPIDIC COMPOUNDS COMPRISING AT LEAST ONE TERMINAL RADICAL OF FORMULA -NH-CX-A OR -NH-CX-NH-A, COMPOSITIONS CONTAINING THEM AND USES THEREOF<br/>[FR] COMPOSÉS LIPIDIQUES COMPRENANT AU MOINS UN RADICAL TERMINAL DE FORMULE -NH-CX-A OU -NH-CX-NH-A, COMPOSITIONS LES CONTENANT ET LEURS UTILISATIONS
  申请人：SANOFI PASTEUR

  公开号：WO2022013443A1

  公开（公告）日：2022-01-20

  The disclosure relates to novel lipidic compounds, lipid nanoparticles (LNPs) containing thereof, and the use of the lipidic compounds or the LNPs for the delivery of nucleic acid. The lipidic compounds as disclosed herein comprise at least one terminal radical of formula (I): *-NH-CX-(NH)n-A (I) wherein: - *- represents a single bond linking said radical of formula (I), directly or not, to to one C10 to C55 lipophilic or hydrophobic tail-group; - n is 0 or 1; - X is an oxygen or sulfur atom, and - A represents an optionally substituted 5- or 6-membered unsaturated heterocyclic radical or 5- or 6-membered heteroaromatic ring radical, both containing at least one nitrogen atom; or one of the pharmaceutically acceptable salts of said radical of formula (I); and with said compound that is in all the possible racemic, enantiomeric and diastereoisomeric isomer forms.

  该披露涉及新型脂质化合物，含有该脂质化合物的脂质纳米颗粒（LNPs），以及利用该脂质化合物或LNPs用于传递核酸。所述的脂质化合物至少包括一个式（I）的末端基团：*-NH-CX-(NH)n-A（I）其中：- *-代表连接所述式（I）的基团的单键，直接或间接地，连接到一个C10至C55的亲脂性或疏水性尾基团；- n为0或1；- X为氧或硫原子，- A代表一个可选择地取代的含有至少一个氮原子的5-或6-成员不饱和杂环基团或5-或6-成员杂芳环基团；或所述的式（I）基团的药学上可接受的盐之一；以及与所述化合物一起，以所有可能的外消旋、对映异构体和顺反异构体形式存在。
• [EN] CLEAVABLE LIPIDIC COMPOUNDS, COMPOSITIONS CONTAINING THEREOF, AND USES THEREOF<br/>[FR] COMPOSÉS LIPIDIQUES CLIVABLES, COMPOSITIONS LES CONTENANT ET UTILISATIONS ASSOCIÉES
  申请人：SANOFI PASTEUR

  公开号：WO2022013439A1

  公开（公告）日：2022-01-20

  The disclosure relates to novel lipidic compounds, method of manufacturing lipid nanoparticles (LNPs) containing thereof, lipid nanoparticles (LNPs) containing thereof, and the use of the LNPs for the delivery of nucleic acid. The lipidic compounds as disclosed herein is a cleavable lipidic compound comprising at least one terminal radical of formula (I): Y-(CHR)n-Z-(CHR')p-Q * (I) wherein: - * is the end linked, directly or not, to one C10 to C55 lipophilic or hydrophobic tail-group; - Y is a radical selected in the group consisting of methyl, methoxy, trifluoromethyl, imidazolyl, or is one hydrogen; - Z is a radical -NH-CH2-CO-O-** or a radical -CR''(NH2)-CO-O-** with ** that is the end closest to Q and R'' that is selected in the group consisting of hydrogen, methyl radical and trifluoromethyl radical; - Q is a radical -NH-CH2-CO-O-*** or a radical -CR''(NH2)-CO-O-*** with R'' selected in the group consisting of hydrogen, methyl radical and trifluoromethyl radical and *** that is the end linked, directly or not, to said lipophilic or hydrophobic tail-group; - R et R' are, independently one from the other, one hydrogen, one methyl radical or one trifluoromethyl radical; - n et p are independently one from the other 0, 1 or 2; or one of its pharmaceutically acceptable salts and with said compound being in all the possible racemic, enantiomeric and diastereoisomeric isomer forms.

  该披露涉及新型脂质化合物，制造含有脂质纳米颗粒（LNPs）的方法，含有脂质纳米颗粒（LNPs），以及将LNPs用于传递核酸。所述的脂质化合物是一种可切割的脂质化合物，包括至少一个式（I）的末端基团：Y-(CHR)n-Z-(CHR')p-Q *（I）其中：- *是末端连接的，直接或间接连接到一个C10至C55的亲脂性或疏水性尾基团；- Y是在甲基，甲氧基，三氟甲基，咪唑基中选择的基团，或是一个氢原子；- Z是一个基团-NH-CH2-CO-O-**或一个基团-CR''(NH2)-CO-O-**，其中**是最接近Q的末端，R''在氢原子，甲基基团和三氟甲基基团中选择；- Q是一个基团-NH-CH2-CO-O-***或一个基团-CR''(NH2)-CO-O-***，其中R''在氢原子，甲基基团和三氟甲基基团中选择，***是直接或间接连接到所述亲脂性或疏水性尾基团的末端；- R和R'是彼此独立的氢原子，甲基基团或三氟甲基基团；- n和p是彼此独立的0、1或2；或其药用可接受的盐，所述化合物以所有可能的外消旋、对映异构体和顄对映异构体形式存在。
• Application of selenosulfonation to marine sterol synthesis. Preparation of 24,28-dehydroaplysterol, xestosterol and ostreasterol from a common acetylenic intermediate
  作者：Thomas G Back、John R Proudfoot、Carl Djerassi

  DOI：10.1016/s0040-4039(00)84483-4

  日期：——

  The title compounds were synthesized from a readily available steroidal acetylene by a protocol employing selenosulfonation, introduction of the appropriate side chain at C-24 via an alkyl selenocuprate, and reductive desulfonylation.

  标题化合物是由易于获得的甾族乙炔通过以下方法合成的：采用硒代磺化，通过硒代烷基磺酸烷基酯在C-24处引入合适的侧链以及还原性脱磺酰化。