(±)-1-[(3aR,4S,9bS)-4-(6-Bromo-1,3-benzodioxol-5-yl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinolin-8-yl]-ethanone | 925419-55-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (±)-1-[(3aR,4S,9bS)-4-(6-Bromo-1,3-benzodioxol-5-yl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinolin-8-yl]-ethanone
• 英文别名: 1-(4-(6-bromobenzo[d][1,3]dioxol-5-yl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinolin-8-yl)ethan-1-one；P4W25NL8MY；1-[(3aR,4S,9bS)-4-(6-bromo-1,3-benzodioxol-5-yl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinolin-8-yl]ethanone
• CAS: 925419-55-2
• 化学式: C₂₁H₁₈BrNO₃
• 分子量: 412.283
• InChiKey: VHSVKVWHYFBIFJ-QTCYRWPVSA-N

物化性质

• 沸点：
  529.6±50.0 °C(Predicted)
• 密度：
  1.457±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (±)-1-[(3aR,4S,9bS)-4-(6-Bromo-1,3-benzodioxol-5-yl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinolin-8-yl]-ethanone 在 column packed with Chrialpak 1A resin 作用下， 以 乙醇 、 甲基叔丁基醚 、 乙酸乙酯 、 二乙胺 为溶剂， 生成 1-((3aS,4R,9bR)-4-(6-bromobenzo[d][1,3]dioxol-5-yl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinolin-8-yl)ethan-1-one camsylate
  参考文献：
  名称：

  ENANTIOMERICALLY PURIFIED GPER ANGONIST FOR USE IN TREATING DISEASE STATES AND CONDITIONS

  摘要：

  本公开提供了1) 一个对映纯化的化合物SRR G-1，或其衍生物，包括特定的晶体形式、盐和共晶，可以调节G蛋白偶联的雌激素受体活性，2) 包含对映纯化的SRR G-1或其衍生物的药用和化妆品组合物，以及3) 用于治疗或预防通过这些受体介导的疾病状态和条件以及人类和动物相关方法的化妆条件的方法。

  公开号：

  US20200024262A1
• 作为产物：
  描述：

  4-氨基苯乙酮 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 乙醇 、 甲基叔丁基醚 、 二乙胺 、 乙腈 为溶剂， 反应 2.0h， 生成 (±)-1-[(3aR,4S,9bS)-4-(6-Bromo-1,3-benzodioxol-5-yl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinolin-8-yl]-ethanone 、 G-1
  参考文献：
  名称：

  ENANTIOMERICALLY PURIFIED GPER ANGONIST FOR USE IN TREATING DISEASE STATES AND CONDITIONS

  摘要：

  本公开提供了1) 一个对映纯化的化合物SRR G-1，或其衍生物，包括特定的晶体形式、盐和共晶，可以调节G蛋白偶联的雌激素受体活性，2) 包含对映纯化的SRR G-1或其衍生物的药用和化妆品组合物，以及3) 用于治疗或预防通过这些受体介导的疾病状态和条件以及人类和动物相关方法的化妆条件的方法。

  公开号：

  US20200024262A1

文献信息

• Microwave-assisted expeditious and efficient synthesis of cyclopentene ring-fused tetrahydroquinoline derivatives using three-component Povarov reaction
  作者：Abhijit R. Kulkarni、Ganesh A. Thakur

  DOI：10.1016/j.tetlet.2013.09.107

  日期：2013.11

  We report here an efficient and expeditious microwave-assisted synthesis of cyclopentadiene ring-fused tetrahydroquinolines using the three-component Povarov reaction catalyzed by indium (III) chloride. This method has an advantage of shorter reaction time (10–15 min) with high and reproducible yields (up to 90%) and is suitable for parallel library synthesis. The optimization process is reported and

  我们在此报告了一种使用由氯化铟 (III) 催化的三组分 Povarov 反应高效快速微波辅助合成环戊二烯环稠合四氢喹啉的方法。该方法的优点是反应时间较短（10-15 分钟），产率高且重现性好（高达 90%），适用于平行库合成。报告了优化过程，并将微波路线的结果与常规合成路线的结果进行了比较。在几乎所有情况下，微波加速始终提供有利于顺式非对映异构体的改进产率。
• Compounds for binding to ERalpha/beta and GPR30, methods of treating disease states and conditions mediated through these receptors and identification thereof
  申请人：Prossnitz Eric R.

  公开号：US20080167334A1

  公开（公告）日：2008-07-10

  The current invention is in the field of molecular biology/pharmacology and provides compounds which modulate the effects of GPR30 as well as the classical estrogen receptors alpha and beta (ERα and ERβ). These compounds may function as agonists and/or antagonists of one or more of the disclosed estrogen receptors. Diseases which are mediated through one or more of these receptors include cancer (particularly breast, reproductive and other hormone-dependent cancers, leukemia, colon cancer, prostate cancer), reproductive (genito-urological) including endometritis, prostatitis, polycystic ovarian syndrome, bladder control, hormone-related disorders, hearing disorders, cardiovascular conditions including hot flashes and profuse sweating, hypertension, stroke, obesity, osteoporosis, hematologic diseases, vascular diseases or conditions such as venous thrombosis, atherosclerosis, among numerous others and disorders of the central and peripheral nervous system, including depression, insomnia, anxiety, multiple sclerosis, neuropathy, neurodegenerative disorders such as Parkinson's disease and Alzheimer's disease, as well as inflammatory bowel disease, Crohn's disease, coeliac (celiac) disease and related disorders of the intestine. A contraceptive indication to prevent or reduce the likelihood of pregnancy after intercourse is a further aspect of the present invention.

  当前的发明涉及分子生物学/药理学领域，并提供调节GPR30以及经典雌激素受体α和β（ERα和ERβ）效应的化合物。这些化合物可能作为抗原或/和拮抗剂作用于所披露的一个或多个雌激素受体。通过这些受体中的一个或多个介导的疾病包括癌症（特别是乳腺、生殖和其他激素依赖性癌症、白血病、结肠癌、前列腺癌）、生殖（泌尿生殖系统）包括子宫内膜炎、前列腺炎、多囊卵巢综合征、膀胱控制、激素相关疾病、听力障碍、心血管疾病包括潮热和大量出汗、高血压、中风、肥胖、骨质疏松症、血液学疾病、血管疾病或情况如静脉血栓形成、动脉粥样硬化等，以及中枢和外周神经系统的疾病，包括抑郁症、失眠、焦虑、多发性硬化、神经病、帕金森病和阿尔茨海默病等神经退行性疾病，以及炎症性肠病、克罗恩病、乳糜泻病和相关肠道疾病。避孕指示以预防或减少性交后怀孕的可能性是本发明的另一个方面。
• Highly efficient synthesis and characterization of the GPR30-selective agonist G-1 and related tetrahydroquinoline analogs
  作者：Ritwik Burai、Chinnasamy Ramesh、Marvin Shorty、Ramona Curpan、Cristian Bologa、Larry A. Sklar、Tudor Oprea、Eric R. Prossnitz、Jeffrey B. Arterburn

  DOI：10.1039/c001307b

  日期：——

  The GPR30 agonist probe G-1 and structural analogs were efficiently synthesized using multicomponent or stepwise Sc(III)-catalyzed aza-Diels–Alder cyclization. Optimization of solvent and reaction temperature provided enhanced endo-diastereoselectivity.

  GPR30激动剂探针G-1及其结构类似物采用多组分或逐步Sc(III)催化的氮-Diels–Alder环化反应高效合成。溶剂和反应温度的优化提高了内顺反异构选择性。
• COMPOUNDS FOR BINDING TO ER ALPHA/BETA AND GPR30, METHODS OF TREATING DISEASE STATES AND CONDITIONS MEDIATED THROUGH THESE RECEPTORS AND IDENTIFICATION THEREOF
  申请人：PROSSNITZ Eric R.

  公开号：US20110092533A1

  公开（公告）日：2011-04-21

  The current invention is in the field of molecular biology/pharmacology and provides compounds which modulate the effects of GPR30 as well as the classical estrogen receptors alpha and beta (ERα and ERβ). These compounds may function as agonists and/or antagonists of one or more of the disclosed estrogen receptors. Diseases which are mediated through one or more of these receptors include cancer (particularly breast, reproductive and other hormone-dependent cancers, leukemia, colon cancer, prostate cancer), reproductive (genito-urological) including endometreitis, prostatitis, polycystic ovarian syndrome, bladder control, hormone-related disorders, hearing disorders, cardiovascular conditions including hot flashes and profuse sweating, hypertension, stroke, obesity, osteoporosis, hematologic diseases, vascular diseases or conditions such as venous thrombosis, atherosclerosis, among numerous others and disorders of the central and peripheral nervous system, including depression, insomnia, anxiety, multiple sclerosis, neuropathy, neurodegenerative disoders such as Parkinson's disease and Alzheimer's disease, as well as inflammatory bowel disease, Crohn's disease, coeliac (celiac) disease and related disorders of the intestine. A contraceptive indication to prevent or reduce the likelihood of pregnancy after intercourse is a further aspect of the present invention.

  当前发明属于分子生物学/药理学领域，提供了调节GPR30及经典雌激素受体α和β（ERα和ERβ）效应的化合物。这些化合物可以作为所披露的一个或多个雌激素受体的激动剂和/或拮抗剂。通过这些受体介导的疾病包括癌症（特别是乳腺、生殖和其他激素依赖性癌症、白血病、结肠癌、前列腺癌）、生殖（泌尿生殖系统）包括子宫内膜炎、前列腺炎、多囊卵巢综合征、膀胱控制、激素相关疾病、听力障碍、心血管疾病包括潮热和大量出汗、高血压、中风、肥胖症、骨质疏松症、血液学疾病、血管疾病或条件如静脉血栓、动脉粥样硬化等等，以及中枢和周围神经系统的疾病，包括抑郁症、失眠、焦虑症、多发性硬化症、神经病、神经退行性疾病如帕金森病和阿尔茨海默病，以及炎症性肠病、克隆病、乳糜泻和相关的肠道疾病。预防或减少性行为后怀孕的避孕适应症是本发明的另一个方面。
• Enantiomerically purified GPER agonist for use in treating disease states and conditions
  申请人：Linnaeus Therapeutics, Inc.

  公开号：US10934277B2

  公开（公告）日：2021-03-02

  The present disclosure provides 1) an enantiomerically purified compound SRR G-1, or a derivative thereof, including specific crystal forms, salts and co-crystals that modulates G protein-coupled estrogen receptor activity, 2) pharmaceutical and cosmetic compositions comprising an enantiomerically purified SRR G-1, or a derivative thereof, and 3) methods of treating or preventing disease states and conditions and cosmetic conditions mediated through these receptors and related methods thereof in humans and animals.

  本公开提供了：1）对映体纯化的化合物 SRR G-1 或其衍生物，包括调节 G 蛋白偶联雌激素受体活性的特定晶体形式、盐和共晶体；2）包含对映体纯化的 SRR G-1 或其衍生物的药物和化妆品组合物；3）在人类和动物中治疗或预防通过这些受体介导的疾病状态和条件以及美容条件的方法及其相关方法。