UC2002 | 162883-06-9

• 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: UC2002
• 英文别名: 3β-ethynyl-3α-hydroxy-5α-pregnan-20-one；3beta-Ethynyl-3alpha-hydroxy-5alpha-pregnan-20-one；1-[(3R,5S,8R,9S,10S,13S,14S,17S)-3-ethynyl-3-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 162883-06-9
• 化学式: C₂₃H₃₄O₂
• 分子量: 342.522
• InChiKey: FGMARUFVNCEQCL-NWWWSWJSSA-N

物化性质

• 沸点：
  446.4±18.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  UC2002 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 以95%的产率得到3β-ethynyl-3α-hydroxy-5α-pregnan-20-one oxime
  参考文献：
  名称：

  NEW STEROIDS HAVING INCREASED WATER SOLUBILITY AND RESISTANCE AGAINST METABOLISM, AND METHODS FOR THEIR PRODUCTION

  摘要：

  揭示了具有增加代谢抵抗力和增加水溶性的类固醇化合物，以及它们的生产方法。这些物质适用于制造用于治疗与类固醇相关或类固醇诱导的中枢神经系统疾病的药物，并用于预防、缓解或治疗此类疾病的方法。

  公开号：

  US20080119416A1
• 作为产物：
  描述：

  20,20-(ethylenedioxy)-5α-pregnan-3-one 在 盐酸 、 乙炔锂乙二胺配合物 作用下， 以 四氢呋喃 、 丙酮 、 苯 为溶剂， 反应 22.0h， 生成 UC2002
  参考文献：
  名称：

  Synthesis and in Vitro Activity of 3β-Substituted-3α-hydroxypregnan-20-ones:  Allosteric Modulators of the GABA_A Receptor

  摘要：

  Two naturally occurring metabolites of progesterone, 3 alpha-hydroxy-5 alpha- and 5 beta-pregnan-20-one (1 and 2), are potent allosteric modulators of the GABA(A) receptor. Their therapeutic potential as anxiolytics, anticonvulsants, and sedative/hypnotics is limited by rapid metabolism. To avoid these shortcomings, a series of 3 beta-substituted derivatives of 1 and 2 was prepared. Small lipophilic groups generally maintain potency in both the 5 alpha- and 5 beta-series as determined by inhibition of [S-35]TBPS binding. In the 5 alpha-series, 3 beta-ethyl, -propyl, -trifluoromethyl and -(benzyloxy)methyl, as well as substituents of the form 3 beta-XCH(2), where X is Cl, Br, or I or contains unsaturation, show limited efficacy in inhibiting [S-35]TBPS binding. In the 5 beta-series, the unsubstituted parent 2 is a two-component inhibitor, whereas all of the 3 beta-substituted derivatives of 2 inhibit TBPS via a single class of binding sites. In addition, all of the 3-substituted 5 beta-sterols tested are full inhibitors of [S-35]TBPS binding. Electrophysiological measurements using alpha 1 beta 2 gamma 2L receptors expressed in oocytes show that 3 beta-methyl- and 3 beta-(azidomethyl)-3 alpha-hydroxy-5 alpha-pregnan-20-one (6 and 22, respectively) are potent full efficacy modulators and that 3 alpha-hydroxy-3 beta-(trifluoromethyl)-5 alpha-pregnan-20-one (24) is a low-efficacy modulator, confirming the results obtained from [S-35]TBPS binding. These results indicate that modification of the 3 beta-position in 1 and 2 maintains activity at the neuroactive steroid site on the GABA(A) receptor. In animal studies, compound 6 (CCD 1042) is an orally active anticonvulsant, while the naturally occurring progesterone metabolites I and 2 are inactive when administered orally, suggesting that 3 beta-substitution slows metabolism of the S-hydroxyl, resulting in orally bioavailable steroid modulators of the GABA(A) receptor.

  DOI：

  10.1021/jm960021x

文献信息

• Method, compositions, and compounds for allosteric modulation of the
  申请人：CoCensys, Inc.

  公开号：US05939545A1

  公开（公告）日：1999-08-17

  Methods, compositions, and compounds for modulating the GABA.sub.A receptor-chloride ionophore complex to alleviate stress, anxiety, seizures, mood disorders, PMS and PND and to induce anesthesia.

  调节GABA-A受体-氯离子载体复合物以缓解压力、焦虑、癫痫、情绪障碍、经前综合征和产后抑郁症，并诱导麻醉的方法、组合物和化合物。
• Process for synthesis of acetylenic carbinols
  申请人：Cocensys, Inc.

  公开号：US05567830A1

  公开（公告）日：1996-10-22

  A method for the preparation of an acetylenic alcohol by reaction of 1,2-dibromoethylene with an alkyl, aryl an heteroaryl lithium in an inert solvent, followed by reaction with a carbonyl-containing compound to give an acetylenic alcohol is disclosed.

  本发明揭示了一种制备乙炔醇的方法，该方法通过在惰性溶剂中将1,2-二溴乙烯与烷基、芳基和杂环基锂反应，然后与含有羰基的化合物反应，以得到乙炔醇。
• [EN] ANDROSTANES AND PREGNANES FOR ALLOSTERIC MODULATION OF GABA RECEPTOR<br/>[FR] ANDROSTANES ET PREGNANES DE MODULATION ALLOSTERIQUE DU RECEPTEUR DU GABA
  申请人：COCENSYS, INC.

  公开号：WO1995021617A1

  公开（公告）日：1995-08-17

  (EN) Methods, compositions, and compounds for modulating the GABAA receptor-chloride ionophore complex to alleviate stress, anxiety, seizures, mood disorders, PMS and PND and to induce anesthesia.(FR) Procédés, compositions et composés de modulation du complexe ionophore chlorure/récepteur du GABAA réduisant le stress, l'angoisse, les crises, la neurasthénie, le syndrome prémenstruel et la dépression postnatale et provoquant l'anesthésie.

  方法，组合物和化合物用于调节GABAA受体-氯离子复合物，以缓解压力、焦虑、癫痫、情绪障碍、月经前综合症和产后抑郁症，并诱导麻醉。
• [EN] ANDROSTANE AND PREGNANE SERIES FOR ALLOSTERIC MODULATION OF GABA RECEPTOR<br/>[FR] SERIES DE L'ANDROSTANE ET DE LA PREGNANE PRODUISANT UNE MODULATION ALLOSTERIQUE DU RECEPTEUR DU GABA
  申请人：COCENSYS, INC.

  公开号：WO1996016076A1

  公开（公告）日：1996-05-30

  (EN) Methods, compositions, and compounds for modulating the GABAA receptor-chloride ionophore complex to alleviate stress, anxiety, seizures, mood disorders, PMS and PND and to induce anesthesia.(FR) Procédés, compositions et composés servant à moduler le complexe ionophore de chlorure et récepteur du GABAA, permettant ainsi d'atténuer le stress, l'anxiété, les crise d'épilepsie, les troubles de l'humeur, la dépression post natale et le syndrome prémenstruel, et de provoquer l'anesthésie.

  (中文) 用于调节GABAA受体-氯离子复合物以缓解压力、焦虑、癫痫、情绪障碍、PMS和PND并诱导麻醉的方法、组合物和化合物。
• Methods for allosteric modulation of the GABA receptor by members of the androstane and pregnane series
  申请人：Cocensys, Inc.

  公开号：US06277838B1

  公开（公告）日：2001-08-21

  Methods, compositions, and compounds for modulating the GABAA receptor-chloride ionophore complex to alleviate stress, anxiety, seizures, mood disorders, PMS and PND and to induce anesthesia.

  用于调节GABAA受体-氯离子复合物的方法、组合物和化合物，以缓解压力、焦虑、癫痫、情绪障碍、经前综合征（PMS）和产后抑郁症（PND），并诱导麻醉。