1-(9-咔唑)-2-氯乙烷酮 | 38002-61-8

• 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
• 中文名称: 1-(9-咔唑)-2-氯乙烷酮
• 英文名称: 1-(9H-carbazol-9-yl)-2-chloroethan-1-one
• 英文别名: 9-(chloroacetyl)-9H-carbazole；1-carbazol-9-yl-2-chloroethanone
• CAS: 38002-61-8
• 化学式: C₁₄H₁₀ClNO
• mdl: MFCD00093938
• 分子量: 243.692
• InChiKey: NIZUEICMEHKRKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(9-咔唑)-2-氯乙烷酮 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以95%的产率得到1-(9H-carbazol-9-yl)-2-iodo-1-ethanone
  参考文献：
  名称：

  New approach to poly(2,7-carbazoles)

  摘要：

  DOI：

  10.1134/s1070363211120176
• 作为产物：
  描述：

  咔唑 、 氯乙酰氯 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以90%的产率得到1-(9-咔唑)-2-氯乙烷酮
  参考文献：
  名称：

  某些取代吩噻嗪及其相关化合物的合成及抗真菌活性

  摘要：

  合成了几种吩噻嗪及其相关化合物，并对其体外抑菌活性进行了评价。对α-氯-N-乙酰基吩噻嗪的观察结果使我们选择该化合物作为抗真菌剂的研究对象。

  DOI：

  10.1016/j.ejmech.2010.10.019

文献信息

• The optimization of a novel selective antagonist for human M2 muscarinic acetylcholine receptor
  作者：Miaomiao Li、Chen Huang、Xingyu Wu、Fan Ding、Zhoumi Hu、Yan Zhu、Lanxue Zhao、Lina Hou、Hongzhuan Chen、Hao Wang、Jianrong Xu、Dewei Tang

  DOI：10.1016/j.bmcl.2020.127632

  日期：2020.12

  Muscarinic acetylcholine receptors (mAChRs) comprise five distinct subtypes denoted M1 to M5. The antagonism of M2 subtype could increase the release of acetylcholine from vesicles into the synaptic cleft and improve postsynaptic functions in the hippocampus via M1 receptor activation, displaying therapeutic potentials for Alzheimer’s disease. However, drug development for M2 antagonists is still challenged

  毒蕈碱型乙酰胆碱受体（mAChRs）包含五个不同的亚型，表示为M 1至M 5。M 2亚型的拮抗作用可通过M 1受体激活增加乙酰胆碱从囊泡向突触间隙的释放并改善海马突触后功能，从而显示出治疗阿尔茨海默氏病的潜力。但是，M 2拮抗剂的药物开发仍在不同的受体亚型中受到挑战。在这项研究中，通过优化虚拟筛选的支架，我们合成了两个聚焦库并生成了多达50个衍生物。通过测量效能和结合选择性，我们发现了新型M 2拮抗剂，配体47，具有亚微摩尔IC 50，高M 2 / M 4选择性（〜30倍）和合适的亲脂性（cLogP = 4.55）。对这些化合物的进一步研究也说明了这种新型支架的结构-活性关系。我们的研究不仅可以提供易于合成的新颖的先导结构，而且还为进一步开发选择性M 2配体提供了有价值的信息。
• Design, Synthesis and Evaluation of Novel 9-substituted Carbazole Derivatives as Potential Anticancer Agents
  作者：Nitin Kumar、Devender Pathak

  DOI：10.2174/1570180812666150430002118

  日期：2015.9.9

  energy. Above mentioned compounds were synthesized by starting with carbazole and characterized by FTIR, 1H-NMR, 13C-NMR, MASS spectrometry and elemental analysis. All the synthesized compounds were evaluated for their anticancer activity by SRB assay method against Human Breast Cancer Line (MCF7). All the tested compounds showed moderate to good anticancer activity. Compound 3d and 6c exhibited highest

  通过分子对接检查了许多咔唑衍生物对拓扑异构酶的抑制特性，该分子对接由ChemDraw软件设计，然后进行3D优化。两个系列，即2-[（4,5-二氢-2-取代苯基）咪唑-1-基氨基] -1-（9H-咔唑-9-基）乙酮（3a-3e）和2-（9H-咔唑-9发现-yl）-N'-[（4-取代苯基）（哌嗪-1-基）]甲基}乙酰肼（6a-6e）具有最小的结合能。通过以咔唑为原料合成上述化合物，并通过FTIR，1 H-NMR，13表征C-NMR，MASS光谱和元素分析。通过SRB测定法评估所有合成的化合物对人乳腺癌细胞系（MCF7）的抗癌活性。所有测试的化合物均显示出中等至良好的抗癌活性。化合物3d和6c显示出对癌细胞系抑制的最高活性。
• Synthesis and biological evaluation of a new series of phenothiazine-containing protein farnesyltransferase inhibitors
  作者：Cristina-Maria Abuhaie、Alina Ghinet、Amaury Farce、Joëlle Dubois、Philippe Gautret、Benoît Rigo、Dalila Belei、Elena Bîcu

  DOI：10.1016/j.ejmech.2012.11.008

  日期：2013.1

  Two new families of human farnesyltransferase inhibitors 13a-m and 14a-d, based on a phenothiazine scaffold, were synthesized. Compounds 14a and 14b were the most promising inhibitors of human farnesyltransferase with IC50 values of 0.7 and 0.6 mu M, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Inhibitory effect of phenothiazine- and phenoxazine-derived chloroacetamides on Leishmania major growth and Trypanosoma brucei trypanothione reductase
  作者：Ana Marcu、Uta Schurigt、Klaus Müller、Heidrun Moll、R. Luise Krauth-Siegel、Helge Prinz

  DOI：10.1016/j.ejmech.2015.11.023

  日期：2016.1

  A number of phenothiazine-, phenoxazine- and related tricyclics-derived chloroacetamides were synthesized and evaluated in vitro for antiprotozoal activities against Leishmania major (L. major) promastigotes. Several analogs were remarkably potent inhibitors, with antileishmanial activities being comparable or superior to those of the reference antiprotozoal drugs. Furthermore, we explored the structure activity relationships of N-10 haloacetamides that influence the potency of such analogs toward inhibition of L major promastigote growth in vitro. With respect to the mechanism of action, selected compounds were evaluated for time -dependent inactivation of Trypanosoma brucei trypanothione reductase. Our results are indicative of a covalent interaction which could account for potent antiprotozoal activities. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Hach; Protiva, Chemicke Listy, 1953, vol. 47, p. 729,730
  作者：Hach、Protiva

  DOI：——

  日期：——