5-(2-chloroethoxy)-2,3-dihydro-1H-inden-1-one | 105920-67-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5-(2-chloroethoxy)-2,3-dihydro-1H-inden-1-one
• 英文别名: 5-(2-chloroethoxy)indan-1-one；5-(β-Chloroethoxy)-1-indanone；5-(2-chloroethoxy)-2,3-dihydroinden-1-one
• CAS: 105920-67-0
• 化学式: C₁₁H₁₁ClO₂
• 分子量: 210.66
• InChiKey: PPUYXFRSZWNWAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  5-(2-chloroethoxy)-2,3-dihydro-1H-inden-1-one 、 4-[(benzylmethylamino)methyl]benzaldehyde 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以43%的产率得到2-{4-[(benzylmethylamino)methyl]benzylidene}-5-(2-chloroethoxy)indan-1-one
  参考文献：
  名称：

  Targeting Alzheimer’s disease: Novel indanone hybrids bearing a pharmacophoric fragment of AP2238

  摘要：

  We report on a series of hybrid compounds structurally derived from donepezil and AP2238. This study was aimed at improving the activities of the reference compounds, donepezil and AP2238, and at broadening the range of activities of new derivatives as, due to the multifactorial nature of AD, molecules that modulate the activity of a single protein target are unable to significantly modify the progression of the disease. In particular, the indanone core from donepezil was linked to the phenyl-N-methylbenzylamino moiety from AP2238, through a double bond that was kept to evaluate the role of a lower flexibility in the biological activities. Moreover, SAR studies were performed to evaluate the role of different substituents in position 5 or 6 of the indanone ring in the interaction with the PAS, introducing also alkyl chains of different lengths carrying different amines at one end. Derivatives 21 and 22 proved to be the most active within the series and their potencies against AChE were in the same order of magnitude of the reference compounds. Compounds 15, 21-22, with a 5-carbon alkyl chain bearing an amino moiety at one end, better contacting the PAS, remarkably improved the inhibition of AChE-induced A beta aggregation with respect to the reference compounds. They also showed activity against self-aggregation of A beta(42) peptide, the most amyloidogenic form of amyloid produced in AD brains, while the reference compounds resulted completely ineffective. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.071
• 作为产物：
  描述：

  5-羟基-1-茚酮 、 1-溴-2-氯乙烷 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以55 %的产率得到5-(2-chloroethoxy)-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  取代茚满酮/苯并呋喃酮和哌啶杂化物的合成和神经保护评价

  摘要：

  基于丁苯酞和多奈哌齐的神经保护作用，设计并合成了一系列茚满酮/苯并呋喃酮和哌啶杂化物，用于评估其神经保护活性，旨在提高天然苯酞类似物的生物利用度和治疗效果。在这项研究中，观察到与苯并呋喃酮化合物相比，大多数尾部带有 1-甲基哌啶的茚满酮衍生物对体外氧糖剥夺/再灌注 (OGD/R) 诱导的大鼠原代神经元细胞损伤模型表现出优异的神经保护作用。在合成的化合物中，11种（ 4、14、15、22、26、35、36、37、48、49和 52 ）在 OGD / R 模型中表现出强大的细胞活力，以及良好的血脑屏障渗透性：通过平行人工膜渗透性测定证实。值得注意的是，化合物4在 3.125 至 100 μM 的浓度范围内表现出显着的神经元细胞活力，且不诱导细胞毒性。体内大脑中动脉闭塞/R实验的进一步结果表明， 4可有效改善缺血再灌注损伤，在40 mg/kg的剂量下将梗塞体积减少至18.45%。这一结果表明，与

  DOI：

  10.1021/acschemneuro.4c00054

文献信息

• Imidazolylethoxyindanes and use as antithrombotic agents
  申请人：Ferrer Internacional, S.A.

  公开号：US04610998A1

  公开（公告）日：1986-09-09

  The invention is concerned with the novel imidazolylethoxy indanes represented by formula (I), ##STR1## or a pharmacologically-acceptable salt thereof, a process for the preparation of them, and a pharmaceutical composition which contains these new compounds as active ingredient and can be used as antithrombotic and platelet antiaggregating agents.

  本发明涉及由公式（I）表示的新型咪唑乙氧基茚烷衍生物，##STR1##或其药学上可接受的盐，其制备过程以及含有这些新化合物作为活性成分的药物组合物，可用作抗血栓和抗血小板聚集剂。
• Imidazolylalkoxyindanic derivatives, a process for preparing them and pharmaceutical composition containing them
  申请人：FERRER INTERNACIONAL, S.A.

  公开号：EP0184809A1

  公开（公告）日：1986-06-18

  The invention relates to imidazolylethoxyindanic derivatives of the general formula (I): wherein X is C=O, CH-CN or CH-COOH and the ether group (-0-) is bonded to the indanic group in the 4-, 5- or 6- position, n is 1 to 4 and the nontoxic addition salts thereof, as well as to a process for preparing these compounds and to pharmaceutical compositions containing these compounds. These compounds are antithrombotic and platelet anti- aggregating agents and are therefore useful in the treatment of cardiovascular diseases, respiratory disorders and inflammatory conditions. Furthermore, these compounds reduce metastasis in a large number of tumors.

  本发明涉及通式（I）的咪唑乙氧基茚满衍生物：其中 X 为 C=O、CH-CN 或 CH-COOH，醚基（-0-）与茚满基键合在 4-、5- 或 6-位，n 为 1 至 4 及其无毒加成盐，以及制备这些化合物的工艺和含有这些化合物的药物组合物。 这些化合物是抗血栓和血小板抗聚集剂，因此可用于治疗心血管疾病、呼吸系统疾病和炎症。 此外，这些化合物还能减少大量肿瘤的转移。
• US4610998A
  申请人：——

  公开号：US4610998A

  公开（公告）日：1986-09-09
• Targeting Alzheimer’s disease: Novel indanone hybrids bearing a pharmacophoric fragment of AP2238
  作者：Stefano Rizzo、Manuela Bartolini、Luisa Ceccarini、Lorna Piazzi、Silvia Gobbi、Andrea Cavalli、Maurizio Recanatini、Vincenza Andrisano、Angela Rampa

  DOI：10.1016/j.bmc.2010.01.071

  日期：2010.3

  We report on a series of hybrid compounds structurally derived from donepezil and AP2238. This study was aimed at improving the activities of the reference compounds, donepezil and AP2238, and at broadening the range of activities of new derivatives as, due to the multifactorial nature of AD, molecules that modulate the activity of a single protein target are unable to significantly modify the progression of the disease. In particular, the indanone core from donepezil was linked to the phenyl-N-methylbenzylamino moiety from AP2238, through a double bond that was kept to evaluate the role of a lower flexibility in the biological activities. Moreover, SAR studies were performed to evaluate the role of different substituents in position 5 or 6 of the indanone ring in the interaction with the PAS, introducing also alkyl chains of different lengths carrying different amines at one end. Derivatives 21 and 22 proved to be the most active within the series and their potencies against AChE were in the same order of magnitude of the reference compounds. Compounds 15, 21-22, with a 5-carbon alkyl chain bearing an amino moiety at one end, better contacting the PAS, remarkably improved the inhibition of AChE-induced A beta aggregation with respect to the reference compounds. They also showed activity against self-aggregation of A beta(42) peptide, the most amyloidogenic form of amyloid produced in AD brains, while the reference compounds resulted completely ineffective. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and Neuroprotective Evaluation of Substituted Indanone/Benzofuranone and Piperidine Hybrids
  作者：Qing Zeng、Ziwei Zhang、Zhifang Cai、Pei Hu、Zunhua Yang、Yang Wan、Huilan Li、Jian Xiong、Yulin Feng、Yuanying Fang

  DOI：10.1021/acschemneuro.4c00054

  日期：——

  Based on the neuroprotection of butylphthalide and donepezil, a series of indanone/benzofuranone and piperidine hybrids were designed and synthesized for assessment of their neuroprotective activities, aiming to enhance the bioavailability and therapeutic efficacy of natural phthalide analogues. Within this study, it was observed that most indanone derivatives bearing 1-methylpiperidine in the tail

  基于丁苯酞和多奈哌齐的神经保护作用，设计并合成了一系列茚满酮/苯并呋喃酮和哌啶杂化物，用于评估其神经保护活性，旨在提高天然苯酞类似物的生物利用度和治疗效果。在这项研究中，观察到与苯并呋喃酮化合物相比，大多数尾部带有 1-甲基哌啶的茚满酮衍生物对体外氧糖剥夺/再灌注 (OGD/R) 诱导的大鼠原代神经元细胞损伤模型表现出优异的神经保护作用。在合成的化合物中，11种（ 4、14、15、22、26、35、36、37、48、49和 52 ）在 OGD / R 模型中表现出强大的细胞活力，以及良好的血脑屏障渗透性：通过平行人工膜渗透性测定证实。值得注意的是，化合物4在 3.125 至 100 μM 的浓度范围内表现出显着的神经元细胞活力，且不诱导细胞毒性。体内大脑中动脉闭塞/R实验的进一步结果表明， 4可有效改善缺血再灌注损伤，在40 mg/kg的剂量下将梗塞体积减少至18.45%。这一结果表明，与