7-(4-chlorobenzoyl)-1H-indoline | 91741-84-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 7-(4-chlorobenzoyl)-1H-indoline
• 英文别名: 7-(4-chlorobenzoyl)indoline；Methanone,(4-chlorophenyl)(2,3-dihydro-1h-indol-7-yl)-；(4-chlorophenyl)-(2,3-dihydro-1H-indol-7-yl)methanone
• CAS: 91741-84-3
• 化学式: C₁₅H₁₂ClNO
• 分子量: 257.719
• InChiKey: ZSHLAMNVYONNDW-UHFFFAOYSA-N

物化性质

• 熔点：
  107-108 °C(Solv: ligroine (8032-32-4))
• 沸点：
  467.6±45.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-(4-chlorobenzoyl)-1H-indoline 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 以69%的产率得到7-(4-氯苯甲酰基)吲哚
  参考文献：
  名称：

  抗炎药。3.2-氨基-3-苯甲酰基苯基乙酸及其类似物的合成和药理学评价。

  摘要：

  已经合成了一系列2-氨基-3-苯甲酰基苯基乙酸（氨苯乙酸）的取代衍生物，并评估了它们的抗炎，止痛和环加氧酶活性。在这些测定中，包括157（4'-氯），158（4'-溴）和182（5-氯，4'-溴）的几种衍生物比消炎痛更有效。

  DOI：

  10.1021/jm00377a001
• 作为产物：
  描述：

  对氯苯甲腈 、 吲哚啉 在 盐酸 、 三氯化铝 、 三氯化硼 作用下， 生成 7-(4-chlorobenzoyl)-1H-indoline
  参考文献：
  名称：

  抗炎药。3.2-氨基-3-苯甲酰基苯基乙酸及其类似物的合成和药理学评价。

  摘要：

  已经合成了一系列2-氨基-3-苯甲酰基苯基乙酸（氨苯乙酸）的取代衍生物，并评估了它们的抗炎，止痛和环加氧酶活性。在这些测定中，包括157（4'-氯），158（4'-溴）和182（5-氯，4'-溴）的几种衍生物比消炎痛更有效。

  DOI：

  10.1021/jm00377a001

文献信息

• Antiinflammatory agents. 3. Synthesis and pharmacological evaluation of 2-amino-3-benzoylphenylacetic acid and analogs
  作者：David A. Walsh、H. Wayne Moran、Dwight A. Shamblee、Ibrahim M. Uwaydah、William J. Welstead、Lawrence F. Sancilio、Warren N. Dannenburg

  DOI：10.1021/jm00377a001

  日期：1984.11

  A series of substituted derivatives of 2-amino-3-benzoylphenylacetic acid (amfenac) has been synthesized and evaluated for antiinflammatory, analgesic, and cyclooxygenase inhibiting activity. Several derivatives including 157 (4'-chloro), 158 (4'-bromo), and 182 (5-chloro, 4'-bromo) were more potent than indomethacin in these assays.

  已经合成了一系列2-氨基-3-苯甲酰基苯基乙酸（氨苯乙酸）的取代衍生物，并评估了它们的抗炎，止痛和环加氧酶活性。在这些测定中，包括157（4'-氯），158（4'-溴）和182（5-氯，4'-溴）的几种衍生物比消炎痛更有效。
• Synthesis and Cyclooxygenase Inhibition of Sulfonamide-Substituted (Dihydro)Pyrrolo[3,2,1-hi]indoles and Their Potential Prodrugs
  作者：Markus Laube、Cemena Gassner、Torsten Kniess、Jens Pietzsch

  DOI：10.3390/molecules24203807

  日期：——

  shown that methylsulfonyl-substituted (dihydro)pyrrolo[3,2,1-hi]indoles represent highly potent and selective COX-2 inhibitors but possess unsuitable pharmacokinetic properties for radiotracer applications. Based on these results, we herein present the development and evaluation of a second series of sulfonamide-substituted (dihydro)pyrrolo[3,2,1-hi]indoles and their conversion into the respective more

  通过放射性标记配体对环加氧酶-2 (COX-2) 进行非侵入性成像对癌症的诊断具有吸引力，并且具有优化药代动力学特征的新型高度仿射导联对未来的发展非常感兴趣。最近的研究结果表明，甲基磺酰基取代的（二氢）吡咯并 [3,2,1-hi] 吲哚是高效和选择性的 COX-2 抑制剂，但具有不适合放射性示踪剂应用的药代动力学特性。基于这些结果，我们在此介绍了第二系列磺酰胺取代的（二氢）吡咯并 [3,2,1-hi] 吲哚的开发和评估，以及它们向各自更亲水的 N-丙酰胺取代类似物的转化。与甲基磺酰基取代的先导物相比，磺酰胺取代的化合物保留了 COX 抑制效力和选择性；然而，高亲脂性可能会阻碍它们未来的使用。N-丙酰胺取代的类似物显示出显着降低的亲脂性，并且正如预期的那样，降低或没有 COX 抑制效力。因此，N-（磺酰基）丙酰胺可被视为潜在的前药，它代表了更复杂的放射性示踪剂开发的潜在方法。
• WALSH, D. A.;MORAN, H. W.;SHAMBLEE, D. A.;UWAYDAH, I. M.;WELSTEAD, W. J. +, J. MED. CHEM., 1984, 27, N 11, 1379-1388
  作者：WALSH, D. A.、MORAN, H. W.、SHAMBLEE, D. A.、UWAYDAH, I. M.、WELSTEAD, W. J. +

  DOI：——

  日期：——
• Diaryl-Substituted (Dihydro)pyrrolo[3,2,1-<i>hi</i>]indoles, a Class of Potent COX-2 Inhibitors with Tricyclic Core Structure
  作者：Markus Laube、Cemena Gassner、Sai Kiran Sharma、Robert Günther、Arne Pigorsch、Jonas König、Martin Köckerling、Frank Wuest、Jens Pietzsch、Torsten Kniess

  DOI：10.1021/acs.joc.5b00537

  日期：2015.6.5

  A new compound class of diaryl-substituted heterocycles with tricyclic dihydropyrrolo[3,2,1-hi]indole and pyrrolo[3,2,1-hi]indole core structures has been designed and was synthesized by a modular sequence of Friedel-Crafts acylation, amide formation, and McMurry cyclization. This synthesis route represents a novel and versatile access toward dihydropyrrolo[3,2,1-hi]indoles and is characterized by good chemical yields and high modularity. From a set of 19 derivatives, 11 candidates were selected for determination of their COX inhibition potency and were found to be selective inhibitors with high affinity to COX-2 (IC50 ranging from 20-2500 nM and negligible inhibition of COX-1). The binding mode of the novel inhibitors in the active side of COX-2 was calculated in silico using the protein ligand docking program GOLD by application of the molecular structures of two compounds derived from X-ray crystallography. Two novel compounds with high affinity to COX-2 (6k = 70 nM, 8e = 60 nM) have a fluoro substituent, making them promising candidates for the development of F-18-radiolabeled COX-2 inhibitors for imaging purposes with positron emission tomography (PET).
• Preparation and pharmacological profile of 7-(α-Azolylbenzyl)-1H-indoles and indolines as new aromatase inhibitors
  作者：Pascal Marchand、Marc Le Borgne、Martina Palzer、Guillaume Le Baut、Rolf W. Hartmann

  DOI：10.1016/s0960-894x(03)00182-3

  日期：2003.5

  Aromatase (P450 arom) is a target of pharmacological interest for the treatment of breast cancer. New series of 7-(alpha-azolylbenzyl)-1H-indoles and indolines were synthesized as non-steroidal inhibitors of P450 arom. Selectivity was studied towards P450 17alpha enzyme. The most active compound, 1-ethyl-7-[(imidazol-1-yl)(4-chlorophenyl)methyl]-1H-indole 12c exhibited promising relative potency (rp) of 336 (rp, of aminoglutethimide = 1) and most of the described azoles were active and selective towards P450 arom. (C) 2003 Elsevier Science Ltd. All rights reserved.