(3S,10R,13S)-3-((tert-butyldiphenylsilyl)oxy)-10,13-dimethyl-3,4,7,8,9,10,11,12,13,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one | 191677-71-1

• 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: (3S,10R,13S)-3-((tert-butyldiphenylsilyl)oxy)-10,13-dimethyl-3,4,7,8,9,10,11,12,13,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one
• 英文别名: 3β-[(tert-butyldiphenylsilyl)oxy]-androst-5-en-17-one；3β-(tert-butyldiphenylsilyloxy)-5-androsten-17-one；3β-(t-butyldiphenylsilyloxy)-5-androstene-17-one；3beta-(t-Butyldiphenylsilyloxy)-5-androstene-17-one；(3S,8R,9S,10R,13S,14S)-3-[tert-butyl(diphenyl)silyl]oxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
• CAS: 191677-71-1
• 化学式: C₃₅H₄₆O₂Si
• 分子量: 526.835
• InChiKey: DDUQHZIMNFAOCD-MJYPGRFCSA-N

物化性质

• 熔点：
  117-120 °C(Solv: ethanol (64-17-5); ligroine (8032-32-4))
• 沸点：
  581.8±50.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.46
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,10R,13S)-3-((tert-butyldiphenylsilyl)oxy)-10,13-dimethyl-3,4,7,8,9,10,11,12,13,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one 在 palladium diacetate 、 platinum on activated charcoal titanium(IV) isopropylate 、 叔丁基过氧化氢 、 lithium aluminium tetrahydride 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 lutidine 、 氢气 、 氧气 、 苄基三甲基氢氧化铵 、 双(三甲基硅烷基)氨基钾 、 lithium diisopropyl amide 作用下， 以 丙酸 为溶剂， 生成 (R)-3-[(3S,8R,9S,10R,13R,14S,15R,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-15-triethylsilanyloxy-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-butyraldehyde
  参考文献：
  名称：

  Synthesis of xestobergsterol A from dehydroepiandrosterone

  摘要：

  Xestobergsterol A, a potent inhibitor of histamine release, has been synthesized from dehydroepiandrosterone in a route that used introduction of a novel 15-oxygen functionality, side-chain construction via the orthoester Claisen rearrangement and TBAF-promoted epimerization-aldol condensation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.042
• 作为产物：
  描述：

  去氢表雄酮 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 、 乙二醇二甲醚 为溶剂， 以70%的产率得到(3S,10R,13S)-3-((tert-butyldiphenylsilyl)oxy)-10,13-dimethyl-3,4,7,8,9,10,11,12,13,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one
  参考文献：
  名称：

  NEUROSTEROID COMPOUNDS

  摘要：

  本发明涉及具有抗凋亡、神经保护和神经生成特性的新型神经类固醇衍生物，其作用于神经系统，以及制备这些衍生物的方法以及它们在治疗和/或预防或改善与神经元凋亡或神经元损伤相关的神经退行性疾病或与凋亡相关或由凋亡导致的疾病，包括但不限于阿尔茨海默病、帕金森病、亨廷顿病、多发性硬化症和肌萎缩侧索硬化症（ALS）、视网膜变性和脱离、由遗传异常引起的周围神经病变、糖尿病、小儿麻痹症、疱疹、艾滋病和化疗、脑外伤、缺血和中风。活性化合物由式（I）表示：其中R1、R2、R3、R4、R5、R6、R7、A、B、X、Y和Z在本发明描述中有定义。本发明还包括包含式（I）中的一个或多个化合物的组合物。

  公开号：

  US20100234335A1

文献信息

• CONTRACEPTIVE AGENTS
  申请人：Blanco Gustavo

  公开号：US20140005132A1

  公开（公告）日：2014-01-02

  The invention provides compounds of formula I, II, III, or IV: wherein R 1 to R 11 , X, and Y have any of the values defined in the specification. The compounds inhibit Na, K-ATPase α4 and are useful as contraceptive agents.

  这项发明提供了式I、II、III或IV的化合物： 其中R1至R11、X和Y具有规范中定义的任何值。这些化合物抑制Na、K-ATPase α4，并可用作避孕剂。
• Synthesis of analogues of linckoside B, a new neuritogenic steroid glycoside
  作者：Qingchao Liu、Yue Yu、Peng Wang、Yingxia Li

  DOI：10.1039/c3nj00514c

  日期：——

  A facile synthetic approach toward six designed analogues (2–7) of linckoside B, a new neuritogenic steroid glycoside isolated from the Okinawan starfish Linckia laevigata, has been developed. The key steroid aglycon was achieved by a dimethylaluminum chloride-mediated ‘ene’ reaction. A versatile strategy was employed for the construction of glycosidic bonds through Schmidt's procedure using a glycosyl trichloroacetimidate donor.

  从冲绳海星 Linckia laevigata 中分离出的一种新的致神经甾体苷--linckoside B 的六种类似物（2-7）的简易合成方法已经开发成功。关键的类固醇苷元是通过二甲基氯化铝介导的 "烯 "反应生成的。通过施密特程序，使用三氯乙酰亚氨酸糖基供体构建糖苷键时，采用了一种多功能策略。
• A quest for the stereo-electronic requirements for selective agonism for the neurotrophin receptors TrkA and TrkB in 17-spirocyclic-dehydroepiandrosterone derivatives
  作者：Daniele Narducci、Despoina Charou、Thanasis Rogdakis、Ioanna Zota、Vivi Bafiti、Maria Zervou、Theodora Katsila、Achille Gravanis、Kyriakos C. Prousis、Ioannis Charalampopoulos、Theodora Calogeropoulou

  DOI：10.3389/fnmol.2023.1244133

  日期：——

  (a) to selectively activate the TrkA receptor and its downstream signaling kinases Akt and Erk1/2 in PC12 cells, protecting these cells from serum deprivation-induced cell death, and (b) to induce phosphorylation of TrkB and to promote cell survival under serum deprivation conditions in NIH3T3 cells stable transfected with the TrkB receptor and primary cortical astrocytes. In addition the metabolic stability

  简介神经营养蛋白系统在神经系统的发育、形态和生存中发挥着关键作用，其失调已在许多神经退行性疾病和神经炎症性疾病中得到体现。神经营养因子 NGF 和 BDNF 是主要的生长因子，可通过高亲和力分别与其特定的原肌球蛋白相关激酶受体（即 TrkA 和 TrkB）结合来防止神经元死亡和突触损失。较差的药代动力学特性阻碍了神经营养素作为治疗剂的使用。我们课题组之前已经合成了BNN27，一种基于脱氢表雄酮的原型小分子，通过激活TrkA受体来模仿NGF。方法为了更好地了解选择性激活TrkA和TrkB受体的立体电子需求，27种新的脱氢表雄酮衍生物承载合成了C17-螺-二氢吡喃或环丁基部分。对新化合物的能力进行了评估：(a) 选择性激活 PC12 细胞中的 TrkA 受体及其下游信号激酶 Akt 和 Erk1/2，保护这些细胞免受血清剥夺诱导的细胞死亡，以及 (b) 诱导TrkB 并促进稳定转染 TrkB 受体和原代皮质星形胶质细胞的
• Novel Dehydroepiandrosterone Derivatives with Antiapoptotic, Neuroprotective Activity
  作者：Theodora Calogeropoulou、Nicolaos Avlonitis、Vassilios Minas、Xanthippi Alexi、Athanasia Pantzou、Ioannis Charalampopoulos、Maria Zervou、Varvara Vergou、Efrosini S. Katsanou、Iakovos Lazaridis、Michael N. Alexis、Achille Gravanis

  DOI：10.1021/jm900468p

  日期：2009.11.12

  DHEA analogues with modifications at positions C3 or 07 were synthesized and evaluated for neuroprotective activity against the neural-crest-derived PC12 cell model of serum deprivation-induced apoptosis. The most potent compounds were the spiro-epoxy derivatives 17 beta-spiro[5-androstene-17, 2'-oxiran]-3 beta-ol (20), (20S)-3 beta,21-dihydroxy-17 beta,20-epoxy-5-pregnene (23), and (20R)-3 beta,21-dihydroxy-17 alpha,20-epoxy-5-pregnene (27) with IG(50) values of 0.19 +/- 0.01, 99.0 +/- 4.6, and 6.4 +/- 0.3 nM, respectively. Analogues 20, 23, and 27, up to the micromolar range of concentrations, were unable to activate estrogen receptor alpha and beta (ER alpha and ER beta) or to interfere with ER-dependent gene expression significantly. In addition, they were unable to stimulate the growth of Ishikawa, MCF-7, and LNCaP cells. Our results suggest that the spiro-epoxyneurosteroid derivatives 20, 23, and 27 may prove to be lead molecules for the synthesis of novel neuroprotective agents.
• A direct stereoselective synthesis of 7β-hydroxytestosterone
  作者：David Labaree、Robert M. Hoyte、Richard B. Hochberg

  DOI：10.1016/s0039-128x(97)00018-4

  日期：1997.6

  Although 7 beta-hydroxytestosterone is a known product androgen metabolism, there are no published methods for its chemical synthesis except from the equally difficult to obtain 7 beta-hydroxy-4-androstene-3,17-dione. We found that several seemingly straightforward routes for its synthesis failed. Consequently, we tried to produce 7 beta-hydroxytestosterone by enzymatic oxidation of 5-androstene-3 beta,7 beta,17 beta-triol with cholesterol oxidase (Brevibacterium sp.), a procedure previously used to synthesize 7 beta-hydroxy-4-cholesten-3-one from 3 beta,7 beta-dihydroxycholesterol (Alexander and Fisher 1995). However, 5-androstene-3 beta,7 beta,17 beta-triol was, at best, a very poor substrate for the enzyme leading to the production of 7 beta-hydroxytestosterone in only trace amounts. Thus, we explored a strategy for the enzymatic synthesis in which a C-8-ester at C-17 (5-androstene-3 beta,7 beta,17 beta-triol 17-caprylate) would serve to mimic the bulky and hydrophobic side chain of cholesterol and thus allow the C-19-steroid to act as an effective substrate. When this ester was incubated with cholesterol oxidase, it was converted efficiently to 7 beta-hydroxytestosterone-17-caprylate. Attempts to remove the ester group by several mild hydrolytic procedures caused elimination of the 7 beta-hydroxyl group; we, therefore, obtained 7 beta-hydroxy-testosterone by incubation of the intermediate ester with porcine lipase. (C) 1997 by Elsevier Science Inc.