4-氨基茚酮 | 51135-91-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 中文名称: 4-氨基茚酮
• 中文别名: 4-氨基-2,3-二氢茚-1-酮；4-氨基-2,3-二氢-1H-茚-1-酮；4-氨基-2,3-二氢茚酮；4-氨基-1-茚满酮；4-氨基-1-茚酮
• 英文名称: 4-amino-2,3-dihydro-1H-inden-1-one
• 英文别名: 4-aminoindan-1-one；4-amino-1-indanone；4-aminoindanone；4-amino-2,3-dihydroinden-1-one
• CAS: 51135-91-2
• 化学式: C₉H₉NO
• mdl: MFCD06656902
• 分子量: 147.177
• InChiKey: HCPYYLKYVRPDKI-UHFFFAOYSA-N

物化性质

• 熔点：
  122-123 °C
• 沸点：
  323.2±31.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2922399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4-氨基茚酮 在 盐酸 、 copper(l) chloride 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 2.0h， 以63%的产率得到4-氯-1-茚满酮
  参考文献：
  名称：

  Tricyclic Pyrazoles. Part 1: Synthesis and Biological Evaluation of Novel 1,4-Dihydroindeno[1,2-c]pyrazol-based Ligands for CB1and CB2 Cannabinoid Receptors

  摘要：

  Cannabinoids receptors, cellular elements of the endocannabinoid system, have been the focus of extensive studies because of their potential functional role in several important physiological and pathological processes. To further evaluate the properties of CB receptors, especially CB1 and CB2 subtypes, we have designed, using SR141716A as a benchmark, a new series of rigid 1-aryl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxamides. Compounds I were synthesized from substituted 1-aryl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxylic acids and requisite amines. The various analogues were assayed for binding both to the brain and peripheral cannabinoid receptors (CB1 and CB2). Seven of the new compounds displayed very high in vitro CB2 binding affinities, especially 1a, 1b, 1c, 1e, 1g, 1h and 1j which showed K-i values of 0.34, 0.225, 0.27, 0.23, 0.385, 0.037 and 0.9 nM, respectively. Compounds 1a, 1b, 1c and 1h showed the highest selectivity for CB2 receptor with K-i(CB1) to K-i(CB2) ratios of 6029, 5635, 5814 and 9810, respectively. Noticeably, 1h exhibited the highest affinity and selectivity for CB2 receptors. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00319-x
• 作为产物：
  描述：

  3-苯丙酰氯 在 三氯化铝 作用下， 生成 4-氨基茚酮
  参考文献：
  名称：

  Ingold; Piggott, Journal of the Chemical Society, 1923, vol. 123, p. 1482,1508

  摘要：

  DOI：

文献信息

• Sulfonamides having antiangiogenic and anticancer activity
  申请人：——

  公开号：US20040157836A1

  公开（公告）日：2004-08-12

  Compounds having methionine aminopeptidase-2 inhibitory (MetAP2) are described. Also described are pharmaceutical compositions comprising the compounds, methods of treatment using the compounds, methods of inhibiting angiogenesis, and methods of treating cancer.

  描述了具有蛋氨酸氨基肽酶-2抑制剂（MetAP2）的化合物。还描述了包括这些化合物的药物组合物、使用这些化合物的治疗方法、抑制血管生成的方法以及治疗癌症的方法。
• Discovery of novel 2,3-dihydro-1H-inden-1-amine derivatives as selective monoamine oxidase B inhibitors
  作者：Shiyu Li、Xiao Lv、Kai Cheng、Yongbing Tian、Xufeng Huang、Haiyan Kong、Yajun Duan、Jihong Han、Chenzhong Liao、Zhouling Xie

  DOI：10.1016/j.bmcl.2019.02.030

  日期：2019.5

  Inhibition of MAO-B has been an effective strategy for the treatment of Parkinson's disease. To find more potent and selective MAO-B inhibitors with novel chemical scaffold, we designed and synthesized a series of new 2,3-dihydro-1H-inden-1-amine derivatives on basis of our previous study. Furthermore, the corresponding structure-activity relationship (SAR) of these compounds is detailedly discussed

  抑制MAO-B已成为治疗帕金森氏病的有效策略。为了找到具有新型化学支架的更有效和选择性的MAO-B抑制剂，我们在先前的研究基础上设计并合成了一系列新的2,3-二氢-1H-茚满-1-胺衍生物。此外，详细讨论了这些化合物的相应结构-活​​性关系（SAR）。化合物L4（IC50 = 0.11μM），L8（IC50 = 0.18μM），L16（IC50 = 0.27μM）和L17（IC50 = 0.48μM）显示出与司来吉兰相似的MAO-B抑制活性。此外，L4，L16和L17也表现出与司来吉兰相当的选择性，表明L4，L16和L17可能是有希望的选择性MAO-B抑制剂，需要进一步研究。
• Novel 1-(prop-2-yn-1-ylamino)-2,3-dihydro-1H-indene-4-thiol derivatives as potent selective human monoamine oxidase B inhibitors: Design, SAR development, and biological evaluation
  作者：Haiyan Kong、Xianshe Meng、Rui Hou、Xiaoxiao Yang、Jihong Han、Zhouling Xie、Yajun Duan、Chenzhong Liao

  DOI：10.1016/j.bmcl.2021.128051

  日期：2021.7

  developing human monoamine oxidase B (hMAO-B) inhibitors as anti-Parkinson’s disease (PD) drugs. However, low efficiency and unwanted side effects of the marketed hMAO-B inhibitors hamper their medical applications, therefore, novel potent selective hMAO-B inhibitors are still of great interest. Herein we report 1-(prop-2-yn-1-ylamino)-2,3-dihydro-1H-indene-4-thiol derivatives as hMAO-B inhibitors, which

  在开发人类单胺氧化酶 B (hMAO-B) 抑制剂作为抗帕金森病 (PD) 药物方面取得了成功。然而，市售 hMAO-B 抑制剂的低效和有害副作用阻碍了它们的医疗应用，因此，新型有效的选择性 hMAO-B 抑制剂仍然很受关注。在此，我们报告了 1-(prop-2-yn-1-ylamino)-2,3-dihydro-1 H -indene-4-thiol 衍生物作为 hMAO-B 抑制剂，它们是通过采用基于片段的药物设计策略设计的将雷沙吉兰与疏水片段连接起来。在合成的 31 种化合物中，K8和K24表现出非常令人鼓舞的 hMAO-B 抑制活性和对 hMAO-A 的选择性，优于雷沙吉兰和 safinamide。体外研究表明K8和K24对神经组织细胞无毒，它们对 ROS 形成和潜在的神经保护活性有相当大的作用。进一步的小鼠行为试验表明，这两种化合物对 MPTP 诱导的 PD 模型小鼠具有良好的治
• [EN] COVALENT TARGETING OF E3 LIGASES<br/>[FR] CIBLAGE COVALENT DES LIGASES E3
  申请人：UNIV CALIFORNIA

  公开号：WO2020076996A1

  公开（公告）日：2020-04-16

  Disclosed herein, inter alia, are compositions and methods for targeting E3 ligases. In an aspect is a targeted protein degrader including 1) a targeted protein binder and 2) an E3 Ubiquitin ligase binder, wherein the E3 Ubiquitin ligase is human RNF4 or human RNF114. In an aspect is provided a pharmaceutical composition including a compound as described herein, including embodiments, and a pharmaceutically acceptable excipient.

  本公开的内容包括针对E3连接酶的组合物和方法。一个方面涉及一种靶向蛋白降解剂，包括1）靶向蛋白结合物和2）E3泛素连接酶结合物，其中E3泛素连接酶为人类RNF4或人类RNF114。另一方面提供了一种包括本文所述化合物的药物组合物，包括实施例和药用可接受的赋形剂。
• Synthesis of haloindenes
  申请人：Wnuk Stanislaw F.

  公开号：US10954178B1

  公开（公告）日：2021-03-23

  The subject invention provides an expedited synthesis of 5, 6, and 7-iodoindenes from the corresponding aminoindan-1-ones in more than 70% yield, employing readily available precursors and reagents. A three-step sequence involves diazotization-iodination of aminoindan-1-one followed by reduction and dehydration. The method has a general character and can be extended for the preparation of various 4-, 5-, 6- or 7-haloindenes using different halogen sources for diazotization-halogenation reaction.

  该发明提供了一种从相应的氨基茚-1-酮中合成5、6和7-碘茚的快速合成方法，收率超过70％，利用易得的前体和试剂。三步序列包括氨基茚-1-酮的重氮化-碘化，随后进行还原和脱水。该方法具有一般性质，可以通过使用不同卤素源进行重氮化-卤代反应来扩展，用于制备各种4、5、6或7-卤代茚。