(-)-(R)-4-oxiranylmethoxy-1H-indole | 154632-91-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (-)-(R)-4-oxiranylmethoxy-1H-indole
• 英文别名: (R)-(-)-4-(2,3-epoxypropoxy)-1H-indole；(-)-4-[((R)-oxiran-2-yl)methoxy]-1H-indole；4-[[(2R)-oxiran-2-yl]methoxy]-1H-indole
• CAS: 154632-91-4
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: CTWQPSSVUYPWOM-MRVPVSSYSA-N

物化性质

• 熔点：
  83-84 °C
• 沸点：
  381.2±12.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  37.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-(R)-4-oxiranylmethoxy-1H-indole 在 三乙胺 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 26.0h， 生成 (+)-N-[(2R)-hydroxy-3-(1H-indol-4-yloxy)-propyl]-N-isobutyl-3,4-dimethoxy-benzenesulfonamide
  参考文献：
  名称：

  Synthesis and biological evaluation of new simple indolic non peptidic HIV Protease inhibitors: The effect of different substitution patterns

  摘要：

  New structurally simple indolic non peptidic HIV Protease inhibitors were synthesized from (S)-glycidol by regioselective methods. Following the concept of targeting the protein backbone, different substitution patterns were introduced onto the common stereodefined isopropanolamine core modifying the type of functional group on the indole, the position of the functional group on the indole and the type of the nitrogen containing group (sulfonamides or perhydroisoquinoline), alternatively. The systematic study on in vitro inhibition activity of such compounds confirmed the general beneficial effect of the 5-indolyl substituents in presence of arylsulfonamide moieties, which furnished activities in the micromolar range. Preliminary docking analysis allowed to identify several key features of the binding mode of such compounds to the protease.

  DOI：

  10.1016/j.bmc.2014.06.055
• 作为产物：
  描述：

  4-羟基吲哚 、 (R)-对甲苯磺酸缩水甘油酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (-)-(R)-4-oxiranylmethoxy-1H-indole
  参考文献：
  名称：

  Design and synthesis of new potent, silent 5-HT1A antagonists by covalent coupling of aminopropanol derivatives with selective serotonin reuptake inhibitors

  摘要：

  Hybrid molecules built up by covalent coupling of aminopropanol derivatives (especially pindolol) with antidepressant drugs like fluoxetine, paroxetine or milnacipran were found to be potent and silent 5-HT1A antagonists (K-B < 1 nM for 7c and 9a). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00619-2

文献信息

• Compounds having effects on serotonin-related systems
  申请人：Eli Lilly and Company

  公开号：US05741789A1

  公开（公告）日：1998-04-21

  A series of hetero-oxy alkanamines are effective pharmaceuticals for the treatment of conditions related to or affected by the reuptake of serotonin and by the serotonin 1.sub.A receptor. The compounds are particularly useful for alleviating the symptoms of nicotine and tobacco withdrawal, and for the treatment of depression and other conditions for which serotonin reuptake inhibitors are used.

  一系列的杂氧烷胺类化合物是治疗与血清素再摄取和血清素1A受体有关或受其影响的疾病的有效药物。这些化合物特别适用于缓解尼古丁和烟草戒断症状，以及治疗抑郁症和其他需要使用血清素再摄取抑制剂的疾病。
• New indolic non-peptidic HIV protease inhibitors from (S)-glycidol: synthesis and preliminary biological activity
  作者：Lucia Chiummiento、Maria Funicello、Paolo Lupattelli、Francesco Tramutola、Pietro Campaner

  DOI：10.1016/j.tet.2009.05.089

  日期：2009.8

  A series of non-peptidic HIV protease inhibitors were synthesized starting from the same optically active precursor, (S)-glycidol. The substrate was easily converted into different indolic sulfonamides or amines by regioselective reactions. The preliminary inhibitory activity was evaluated.

  从相同的旋光前体（S）-缩水甘油开始合成了一系列非肽类HIV蛋白酶抑制剂。通过区域选择性反应，底物容易转化为不同的吲哚磺酰胺或胺。评价初步抑制活性。
• Synthesis and adrenolytic activity of 1-(1H-indol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol and its enantiomers. Part 1
  作者：Grażyna Groszek、Marek Bednarski、Małgorzata Dybała、Barbara Filipek

  DOI：10.1016/j.ejmech.2008.05.019

  日期：2009.2

  The synthesis of (2RS)-1-(1H-indol-4-yloxy)-3-[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol ((RS)-9) and its enantiomers has been described and tested for electrocardiographic, antiarrhythmic, hypotensive and spasmolytic activities as well as for α1-, α2- and β1-adrenoceptors' binding affinities. All compounds significantly decrease systolic and diastolic blood pressure, and possess antiarrhythmic

  （2RS）-1-（1H-吲哚-4-基氧基）-3-[2-（2-甲氧基苯氧基）乙基]氨基}丙烷-2-醇（（RS）-9）的合成及其对映异构体进行了描述和测试心电图，抗心律不齐，降血压和解痉活动以及为α 1 - ，α 2 -和β 1肾上腺素能受体的结合亲和性。所有化合物显著降低收缩压和舒张压，并具有抗心律不齐活性和亲和力与α 1 - ，α 2 -和β 1-肾上腺素受体。结果表明，这些化合物的抗心律失常和降压作用与其肾上腺皮质激素的性质有关，但与痉挛性质无关。
• BRIDGED ARYL PIPERAZINES DERIVATIVES USEFUL FOR THE TREATMENT OF CNS, GI-URINARY AND REPRODUCTIVE DISORDERS
  申请人：Creighton J. Christopher

  公开号：US20080070919A1

  公开（公告）日：2008-03-20

  The present invention is directed to bridged aryl piperazine derivatives, pharmaceutical compositions containing them and their use in the treatment of depression and related disorders. The compounds of the present invention are serotonin transport inhibitors and/or modulators of 5HT 1A .

  本发明涉及桥联芳基哌嗪衍生物，含有它们的药物组合物以及它们在治疗抑郁症和相关疾病中的用途。本发明的化合物是血清素转运抑制剂和/或5HT1A的调节剂。
• Synthesis and Pharmacological Activity of a New Series of 1-(1<i>H</i>-Indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propan-2-ol Analogs
  作者：Marek Bednarski、Monika Otto、Magdalena Dudek、Marcin Kołaczkowski、Adam Bucki、Agata Siwek、Grażyna Groszek、Elżbieta Maziarz、Piotr Wilk、Jacek Sapa

  DOI：10.1002/ardp.201500234

  日期：2016.3

  different mechanisms, such as nitric oxide (NO) release, β2‐agonistic action, α1‐blockade, antioxidant action, and Ca2+ entry blockade. Here, a study on evaluation of the cardiovascular activity of five new compounds is presented. Compound 3a is a methyl and four of the tested compounds (3b–e) are dimethoxy derivatives of 1‐(1H‐indol‐4‐yloxy)‐3‐(2‐(2‐methoxyphenoxy)ethylamino)propan‐2‐ol. The obtained results

  β-肾上腺素能受体拮抗剂是治疗心血管疾病的重要疗法。在β-受体阻滞剂组中，除抑制β-肾上腺素能受体外，还具有重要辅助特性的第三代药物备受关注。这些药物的血管舒张活性是通过不同的机制产生的，例如一氧化氮 (NO) 释放、β2 激动作用、α1 阻断、抗氧化作用和 Ca2+ 进入阻断。在这里，介绍了对五种新化合物的心血管活性评估的研究。化合物 3a 是甲基，四个测试化合物 (3b-e) 是 1-(1H-indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propan-2-ol 的二甲氧基衍生物。