6-Pyrrolidino-1-indanon | 3133-96-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 6-Pyrrolidino-1-indanon
• 英文别名: 6-Pyrrolidin-1-yl-2,3-dihydroinden-1-one；6-pyrrolidin-1-yl-2,3-dihydroinden-1-one
• CAS: 3133-96-8
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: QFSKHOKWMNNWAE-UHFFFAOYSA-N

物化性质

• 沸点：
  381.9±31.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-Pyrrolidino-1-indanon 、 3-甲氧基-4-[(四氢-2H-吡喃-2-基)氧基]苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  新型查耳酮类化合物作为有效且可逆的胰脂肪酶抑制剂的设计、合成和生物学评价

  摘要：

  胰腺脂肪酶 (PL) 是一种负责水解膳食脂质的关键酶，已被证实是预防和治疗肥胖相关代谢紊乱的关键治疗靶点。在此，我们报告了一系列作为有效和可逆 PL 抑制剂的查耳酮类化合物的设计、合成和生物学评价。在类查尔酮骨架的 A 环和 B 环处进行两轮结构修饰后，研究了类查耳酮化合物的结构-PL 抑制关系，同时揭示了有利于 PL 抑制的关键取代基。在所有测试的查尔酮类化合物中，化合物B13（一种新型查尔酮类化合物，带有两条长碳链）显示出最有效的 PL 抑制活性，IC 500.33 μM 的值。抑制动力学分析表明，B13可以以混合抑制方式有效抑制 PL 介导的 4-MUO 水解，K i值为 0.12 μM。分子对接模拟表明，B13可以在催化位点和位于 PL 表面的非催化位点与 PL 紧密结合，这与该试剂的混合抑制模式一致。此外，B13在人工胃肠液中表现出优异的稳定性，在人肝制剂中表现出良好的代谢稳定性

  DOI：

  10.1016/j.bmc.2020.115853
• 作为产物：
  描述：

  6-溴茚酮 在 咪唑 、 palladium diacetate 、 sodium tetrahydroborate 、 草酰氯 、 三叔丁基膦 、 四丁基氟化铵 、 二甲基亚砜 、 三乙胺 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 6-Pyrrolidino-1-indanon
  参考文献：
  名称：

  The discovery and synthesis of novel adenosine receptor (A2A) antagonists

  摘要：

  In high throughput screening of our file compounds, a novel structure 1 was identified as a potent A(2A) receptor antagonist with no selectivity over the A(1) adenosine receptor. The structure-activity relationship investigation using 1 as a template lead to identification of a novel class of compounds as potent and selective antagonists of A(2A) adenosine receptor. Compound 26 was identified to be the most potent A(2A) receptor antagonist (K-i = 0.8 nM) with 100-fold selectivity over the A(1) adenosine receptor. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.019

文献信息

• Design, synthesis and biological evaluation of indanone–chalcone hybrids as potent and selective hCES2A inhibitors
  作者：Peng-Chao Huo、Xiao-Qing Guan、Peng Liu、Yun-Qing Song、Meng-Ru Sun、Rong-Jing He、Li-Wei Zou、Li-Juan Xue、Jin-Hui Shi、Nan Zhang、Zhi-Guo Liu、Guang-Bo Ge

  DOI：10.1016/j.ejmech.2020.112856

  日期：2021.1

  ester-bearing drugs. Accumulating evidence has indicated that hCES2A inhibitor therapy can modulate the pharmacokinetic and toxicological profiles of some important hCES2A-substrate drugs, such as the anticancer agent CPT-11. Herein, a series of indanone–chalcone hybrids are designed and synthesized to find potent and highly selective hCES2A inhibitors. Inhibition assays demonstrated that most indanone–chalcone

  人羧酸酯酶2（hCES2A）是分布在小肠中的主要丝氨酸水解酶之一，在含酯药物的水解中起关键作用。越来越多的证据表明，hCES2A抑制剂疗法可以调节某些重要的hCES2A底物药物（例如抗癌药CPT-11）的药代动力学和毒理学特征。本文设计并合成了一系列茚满酮-查耳酮杂化物，以发现有效且高度选择性的hCES2A抑制剂。抑制分析表明，大多数茚满酮-查耳酮杂种均表现出强至中等的hCES2A抑制活性。结构-hCES2A抑制活性关系研究表明，在C4'位引入羟基和在C6位引入N-烷基对于hCES2A抑制是有益的。尤其，B7（N-烷基化的1-茚满酮-查尔酮杂化物）对hCES2A表现出最强的抑制作用，并具有出色的特异性（该试剂不能抑制其他人类酯酶，包括hCES1A和丁酰胆碱酯酶）。抑制动力学分析表明，B7以混合抑制方式有效抑制hCES2A介导的FD水解。K i值为0.068μM。此外，B7能够抑制活细胞中的
• Design, synthesis, and structure–activity relationships of 2-benzylidene-1-indanone derivatives as anti-inflammatory agents for treatment of acute lung injury
  作者：Siyang Xiao、Wenxin Zhang、Hongjin Chen、Bo Fang、Yinda Qiu、Xianxin Chen、Lingfeng Chen、Shen Shu、Yali Zhang、Yunjie Zhao、Zhiguo Liu、Guang Liang

  DOI：10.2147/dddt.s160314

  日期：——

  Purpose: The purpose of this study was to design and synthesize novel 2-benzylidene-1-indanone derivatives for treatment of acute lung injury.Methods: A series of 39 novel 2-benzylidene-indanone structural derivatives were synthesized and evaluated for anti-inflammatory activity in lipopolysaccharide (LPS)-stimulated murine primary macrophages.Results: Most of the obtained compounds effectively inhibited the LPS-induced expression of IL-6 and TNF-alpha. The most active compound, 8f, was found to significantly reduce LPS-induced pulmonary inflammation, as reflected by reductions in the concentration of total protein, inflammatory cell count, as well as the lung wet/dry ratio in bronchoalveolar lavage (BAL) fluid. Furthermore, 8f effectively inhibited mRNA expression of several inflammatory cytokines after LPS challenge in vitro and in vivo. Administration of 8f also blocked LPS-induced activation of the proinflammatory NF-kappa B/MAPK signaling pathway.Conclusion: The simple synthetic preparation and biological properties of these derivatives make these 2-benzylidene-indanone scaffolds promising new entities for the development of anti-inflammatory therapeutics for the treatment of acute lung injury.
• Design, synthesis and biological evaluation of novel chalcone-like compounds as potent and reversible pancreatic lipase inhibitors
  作者：Peng-Chao Huo、Qing Hu、Sheng Shu、Qi-Hang Zhou、Rong-Jing He、Jie Hou、Xiao-Qing Guan、Dong-Zhu Tu、Xu-Dong Hou、Peng Liu、Nan Zhang、Zhi-Guo Liu、Guang-Bo Ge

  DOI：10.1016/j.bmc.2020.115853

  日期：2021.1

  obesity-associated metabolic disorders. Herein, we report the design, synthesis and biological evaluation of a series of chalcone-like compounds as potent and reversible PL inhibitors. Following two rounds of structural modifications at both A and B rings of a chalcone-like skeleton, structure-PL inhibition relationships of the chalcone-like compounds were studied, while the key substituents that would be beneficial

  胰腺脂肪酶 (PL) 是一种负责水解膳食脂质的关键酶，已被证实是预防和治疗肥胖相关代谢紊乱的关键治疗靶点。在此，我们报告了一系列作为有效和可逆 PL 抑制剂的查耳酮类化合物的设计、合成和生物学评价。在类查尔酮骨架的 A 环和 B 环处进行两轮结构修饰后，研究了类查耳酮化合物的结构-PL 抑制关系，同时揭示了有利于 PL 抑制的关键取代基。在所有测试的查尔酮类化合物中，化合物B13（一种新型查尔酮类化合物，带有两条长碳链）显示出最有效的 PL 抑制活性，IC 500.33 μM 的值。抑制动力学分析表明，B13可以以混合抑制方式有效抑制 PL 介导的 4-MUO 水解，K i值为 0.12 μM。分子对接模拟表明，B13可以在催化位点和位于 PL 表面的非催化位点与 PL 紧密结合，这与该试剂的混合抑制模式一致。此外，B13在人工胃肠液中表现出优异的稳定性，在人肝制剂中表现出良好的代谢稳定性
• The discovery and synthesis of novel adenosine receptor (A2A) antagonists
  作者：Julius J. Matasi、John P. Caldwell、Jinsong Hao、Bernard Neustadt、Leyla Arik、Carolyn J. Foster、Jean Lachowicz、Deen B. Tulshian

  DOI：10.1016/j.bmcl.2005.01.019

  日期：2005.3

  In high throughput screening of our file compounds, a novel structure 1 was identified as a potent A(2A) receptor antagonist with no selectivity over the A(1) adenosine receptor. The structure-activity relationship investigation using 1 as a template lead to identification of a novel class of compounds as potent and selective antagonists of A(2A) adenosine receptor. Compound 26 was identified to be the most potent A(2A) receptor antagonist (K-i = 0.8 nM) with 100-fold selectivity over the A(1) adenosine receptor. (c) 2005 Elsevier Ltd. All rights reserved.