1-(5-bromo-1H-indol-1-yl)-2-chloroethanone | 1318251-99-8

• 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
• 英文名称: 1-(5-bromo-1H-indol-1-yl)-2-chloroethanone
• 英文别名: 5-bromo-1-(chloroacetyl)-1H-indole；1-(5-bromoindol-1-yl)-2-chloroethanone
• CAS: 1318251-99-8
• 化学式: C₁₀H₇BrClNO
• mdl: MFCD30720731
• 分子量: 272.529
• InChiKey: ZZPQURQKRPAHFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  4-cyclopropyl-5-pyridin-3-yl-2,4-dihydro-[1,2,4]triazole-3-thione 、 1-(5-bromo-1H-indol-1-yl)-2-chloroethanone 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Narrow SAR in odorant sensing Orco receptor agonists

  摘要：

  The systematic exploration of a series of triazole-based agonists of the cation channel insect odorant receptor is reported. The structure-activity relationships of independent sections of the molecules are examined. Very small changes to the compound structure were found to exert a large impact on compound activity. Optimal substitutions were combined using a 'mix-and-match' strategy to produce best-in-class compounds that are capable of potently agonizing odorant receptor activity and may form the basis for the identification of a new mode of insect behavior modification. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.081
• 作为产物：
  描述：

  5-溴吲哚 、 氯乙酰氯 以 甲苯 为溶剂， 以65 %的产率得到1-(5-bromo-1H-indol-1-yl)-2-chloroethanone
  参考文献：
  名称：

  Synthesis of Indole‐Linked Thiadiazoles and their Anticancer Action against Triple‐Negative Breast Cancer

  摘要：

  摘要三阴性乳腺癌（TNBC）缺乏靶向治疗，且转移率、异质性和复发率明显较高，给治疗带来了巨大挑战，需要更多的化疗干预措施。本研究合成了吲哚类噻二唑衍生物，并筛选了其对三阴性乳腺癌 MDA-MB-231 细胞系的抗增殖效力。化合物 4 h 具有氯苯基，在细胞活力实验中显示出最佳的抗癌效力（IC50：0.43 μM）。标题化合物与表皮生长因子受体（PDB ID：3POZ）的对接能力很强，验证了其体外抗增殖作用。吲哚类杂交化合物的对接得分很高（-9.9 至 -8.7 kcal/mol），显示出与共晶体配体 TAK-285 相当的结合倾向，并在指定受体的活性域中占据类似的战略地位。通过 DFT 评估了集成模板的量子和电子特性，推导出的全局反应性指数（如能隙、电负性、电离电位、化学势、亲电性等）的最佳值表明它们具有合适的生化反应性。这些吲哚杂化物在硅学研究中显示出接近适当的药代动力学效力和生物利用度，表明它们具有潜在的药物用途。吲哚共轭物在体外抗癌作用和结合界面方面前景看好，有望成为解决 TNBC 困境的潜在线索。

  DOI：

  10.1002/cbdv.202302000

文献信息

• Narrow SAR in odorant sensing Orco receptor agonists
  作者：Ian M. Romaine、Robert W. Taylor、Samsudeen P. Saidu、Kwangho Kim、Gary A. Sulikowski、Laurence J. Zwiebel、Alex G. Waterson

  DOI：10.1016/j.bmcl.2014.04.081

  日期：2014.6

  The systematic exploration of a series of triazole-based agonists of the cation channel insect odorant receptor is reported. The structure-activity relationships of independent sections of the molecules are examined. Very small changes to the compound structure were found to exert a large impact on compound activity. Optimal substitutions were combined using a 'mix-and-match' strategy to produce best-in-class compounds that are capable of potently agonizing odorant receptor activity and may form the basis for the identification of a new mode of insect behavior modification. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of Indole‐Linked Thiadiazoles and their Anticancer Action against Triple‐Negative Breast Cancer
  作者：Renu Gavadia、Jyoti Rasgania、Neetu Sahu、Surendra Nimesh、Lacy Loveleen、Satbir Mor、Komal Jakhar

  DOI：10.1002/cbdv.202302000

  日期：2024.4

  With a lack of targeted therapy and significantly high metastasis, heterogeneity, and relapse rates, Triple‐Negative Breast Cancer (TNBC) offers substantial treatment challenges and demands more chemotherapeutic interventions. In the present study, indole‐endowed thiadiazole derivatives have been synthesized and screened for antiproliferative potency against the triple‐negative breast cancer MDA‐MB‐231 cell line. Compound 4 h, possessing chlorophenyl moiety, displays the best anticancer potency (IC₅₀: 0.43 μM) in the cell viability assay. The title compounds demonstrate substantial docking competency against the EGFR receptor (PDB ID: 3POZ), validating their in‐vitro ant proliferative action. With a high docking score (−9.9 to −8.7 kcal/mol), the indole hybrids display significant binding propensity comparable to the co‐crystallized ligand TAK‐285 and occupy a similar strategic position in the active domain of the designated receptor. The quantum and electronic properties of the integrated templates are evaluated through DFT, and optimal values of the deduced global reactivity indices, such as energy gap, electronegativity, ionization potential, chemical potential, electrophilicity, etc., suggest their apt biochemical reactivity. The indole hybrids show near‐appropriate pharmacokinetic efficacy and bioavailability in the in‐silico studies, indicating their candidacy for potential drug usage. Promising in‐vitro anticancer action and binding interfaces project indole conjugates as potential leads in addressing the TNBC dilemma.

  摘要三阴性乳腺癌（TNBC）缺乏靶向治疗，且转移率、异质性和复发率明显较高，给治疗带来了巨大挑战，需要更多的化疗干预措施。本研究合成了吲哚类噻二唑衍生物，并筛选了其对三阴性乳腺癌 MDA-MB-231 细胞系的抗增殖效力。化合物 4 h 具有氯苯基，在细胞活力实验中显示出最佳的抗癌效力（IC50：0.43 μM）。标题化合物与表皮生长因子受体（PDB ID：3POZ）的对接能力很强，验证了其体外抗增殖作用。吲哚类杂交化合物的对接得分很高（-9.9 至 -8.7 kcal/mol），显示出与共晶体配体 TAK-285 相当的结合倾向，并在指定受体的活性域中占据类似的战略地位。通过 DFT 评估了集成模板的量子和电子特性，推导出的全局反应性指数（如能隙、电负性、电离电位、化学势、亲电性等）的最佳值表明它们具有合适的生化反应性。这些吲哚杂化物在硅学研究中显示出接近适当的药代动力学效力和生物利用度，表明它们具有潜在的药物用途。吲哚共轭物在体外抗癌作用和结合界面方面前景看好，有望成为解决 TNBC 困境的潜在线索。