2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamide | 58779-63-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamide
• 英文别名: 2-oxo-1H-benzo[cd]indole-6-sulfonamide
• CAS: 58779-63-8
• 化学式: C₁₁H₈N₂O₃S
• mdl: MFCD02642946
• 分子量: 248.262
• InChiKey: IAAAAIVRZUVFHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamide 、 diethyl 1,1-difluoro-6-iodohexylphosphonate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以59%的产率得到diethyl 1,1-difluoro-4-(2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamido)-hexyl-phosphonate
  参考文献：
  名称：

  Virtual screening, selection and development of a benzindolone structural scaffold for inhibition of lumazine synthase

  摘要：

  Virtual screening of a library of commercially available compounds versus the structure of Mycobacterium tuberculosis lumazine synthase identified 2-(2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamido)acetic acid ( 9) as a possible lead compound. Compound 9 proved to be an effective inhibitor of M. tuberculosis lumazine synthase with a K-i of 70 mu M. Lead optimization through replacement of the carboxymethylsulfonamide sidechain with sulfonamides substituted with alkyl phosphates led to a four-carbon phosphate 38 that displayed a moderate increase in enzyme inhibitory activity (K-i 38 mu M). Molecular modeling based on known lumazine synthase/inhibitor crystal structures suggests that the main forces stabilizing the present benzindolone/enzyme complexes involve pi-pi stacking interactions with Trp27 and hydrogen bonding of the phosphates with Arg128, the backbone nitrogens of Gly85 and Gln86, and the side chain hydroxyl of Thr87. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.072
• 作为产物：
  描述：

  2-氧代-1,2-二氢苯并[cd]吲哚-6-磺酰氯 在 氨 作用下， 以 四氢呋喃 为溶剂， 以79%的产率得到2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamide
  参考文献：
  名称：

  Virtual screening, selection and development of a benzindolone structural scaffold for inhibition of lumazine synthase

  摘要：

  Virtual screening of a library of commercially available compounds versus the structure of Mycobacterium tuberculosis lumazine synthase identified 2-(2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamido)acetic acid ( 9) as a possible lead compound. Compound 9 proved to be an effective inhibitor of M. tuberculosis lumazine synthase with a K-i of 70 mu M. Lead optimization through replacement of the carboxymethylsulfonamide sidechain with sulfonamides substituted with alkyl phosphates led to a four-carbon phosphate 38 that displayed a moderate increase in enzyme inhibitory activity (K-i 38 mu M). Molecular modeling based on known lumazine synthase/inhibitor crystal structures suggests that the main forces stabilizing the present benzindolone/enzyme complexes involve pi-pi stacking interactions with Trp27 and hydrogen bonding of the phosphates with Arg128, the backbone nitrogens of Gly85 and Gln86, and the side chain hydroxyl of Thr87. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.072

文献信息

• METHODS FOR TREATING CANCER WITH RORgamma INHIBITORS
  申请人：The Regents of the University of California

  公开号：EP3268087A1

  公开（公告）日：2018-01-17
• SELF-EMULSIFYING FORMULATIONS OF DIM-RELATED INDOLES
  申请人：Bioresponse LLC

  公开号：EP3280398A1

  公开（公告）日：2018-02-14
• [EN] METHODS FOR TREATING CANCER WITH RORgamma INHIBITORS<br/>[FR] MÉTHODES DE TRAITEMENT DU CANCER PAR DES INHIBITEURS DE ROR GAMMA
  申请人：UNIV CALIFORNIA

  公开号：WO2016145298A1

  公开（公告）日：2016-09-15

  The present invention provides compositions, methods, and kits comprising one or more RORγ inhibitors, alone or in combination with one or more anticancer drugs, such as an anti-androgen drug, that are useful for treating cancer, e.g., prostate cancer, such as castration-resistant prostate cancer (CRPC), and numerous other types of cancer including lung cancer, breast cancer, liver cancer, ovarian cancer, endometrial cancer, bladder cancer, colon cancer, lymphoma, and glioma.
• [EN] SELF-EMULSIFYING FORMULATIONS OF DIM-RELATED INDOLES<br/>[FR] FORMULATIONS AUTO-ÉMULSIFIANTES D'INDOLES ASSOCIÉS AU DIM
  申请人：BIORESPONSE LLC

  公开号：WO2016164770A1

  公开（公告）日：2016-10-13

  Disclosed herein are self-emulsifying compositions and formulations of Dimdolylmethane ("DIM") and certain derivatives of DIM, their uses and methods of making. In particular, the disclosed compositions comprise a DIM-related indole as an active agent and a carrier, wherein the carrier comprises a solvent, one or more surfactants with an HLB of greater than 7, and one or more co-surfactants with an HLB equal to or less than 7. In certain aspects of the invention, the compositions disclosed herein show improved bioavailability.
• Virtual screening, selection and development of a benzindolone structural scaffold for inhibition of lumazine synthase
  作者：Arindam Talukdar、Ekaterina Morgunova、Jianxin Duan、Winfried Meining、Nicolas Foloppe、Lennart Nilsson、Adelbert Bacher、Boris Illarionov、Markus Fischer、Rudolf Ladenstein、Mark Cushman

  DOI：10.1016/j.bmc.2010.03.072

  日期：2010.5

  Virtual screening of a library of commercially available compounds versus the structure of Mycobacterium tuberculosis lumazine synthase identified 2-(2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamido)acetic acid ( 9) as a possible lead compound. Compound 9 proved to be an effective inhibitor of M. tuberculosis lumazine synthase with a K-i of 70 mu M. Lead optimization through replacement of the carboxymethylsulfonamide sidechain with sulfonamides substituted with alkyl phosphates led to a four-carbon phosphate 38 that displayed a moderate increase in enzyme inhibitory activity (K-i 38 mu M). Molecular modeling based on known lumazine synthase/inhibitor crystal structures suggests that the main forces stabilizing the present benzindolone/enzyme complexes involve pi-pi stacking interactions with Trp27 and hydrogen bonding of the phosphates with Arg128, the backbone nitrogens of Gly85 and Gln86, and the side chain hydroxyl of Thr87. (C) 2010 Elsevier Ltd. All rights reserved.