2-bromo-6-(3-methoxybenzyl)-4-methyl-4H-thieno[2',3':4,5]pyrrolo[2,3-d]pyridazin-5(6H)-one | 1222839-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡咯类
• 英文名称: 2-bromo-6-(3-methoxybenzyl)-4-methyl-4H-thieno[2',3':4,5]pyrrolo[2,3-d]pyridazin-5(6H)-one
• 英文别名: 2-Bromo-6-(3-methoxybenzyl)-4-methyl-4,6-dihydro-5H-thieno[2',3':4,5]pyrrolo[2,3-d]pyridazin-5-one；4-bromo-10-[(3-methoxyphenyl)methyl]-7-methyl-3-thia-7,10,11-triazatricyclo[6.4.0.02,6]dodeca-1(8),2(6),4,11-tetraen-9-one
• CAS: 1222839-26-0
• 化学式: C₁₇H₁₄BrN₃O₂S
• 分子量: 404.287
• InChiKey: SPXIMGWYLMAPCS-UHFFFAOYSA-N

物化性质

• 沸点：
  598.2±60.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  75.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-bromo-6-(3-methoxybenzyl)-4-methyl-4H-thieno[2',3':4,5]pyrrolo[2,3-d]pyridazin-5(6H)-one 、 2-苄基-4,4,5,5-四甲基-1,3,2-二杂氧戊硼烷 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以20 mg的产率得到2-benzyl-6-(3-methoxybenzyl)-4-methyl-4H-thieno[2',3':4,5]pyrrolo[2,3-d]pyridazin-5(6H)-one
  参考文献：
  名称：

  WO2020167976A5

  摘要：

  公开号：

  WO2020167976A5
• 作为产物：
  描述：

  2-溴-4H-噻吩并[3,2-b]吡咯-5-羧酸乙酯 在 potassium tert-butylate 、 sodium hydride 、 一水合肼 、 三氯氧磷 作用下， 以 乙二醇甲醚 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 2-bromo-6-(3-methoxybenzyl)-4-methyl-4H-thieno[2',3':4,5]pyrrolo[2,3-d]pyridazin-5(6H)-one
  参考文献：
  名称：

  WO2020167976A5

  摘要：

  公开号：

  WO2020167976A5

文献信息

• Evaluation of thieno[3,2-b]pyrrole[3,2-d]pyridazinones as activators of the tumor cell specific M2 isoform of pyruvate kinase
  作者：Jian-kang Jiang、Matthew B. Boxer、Matthew G. Vander Heiden、Min Shen、Amanda P. Skoumbourdis、Noel Southall、Henrike Veith、William Leister、Christopher P. Austin、Hee Won Park、James Inglese、Lewis C. Cantley、Douglas S. Auld、Craig J. Thomas

  DOI：10.1016/j.bmcl.2010.04.015

  日期：2010.6

  Cancer cells have distinct metabolic needs that are different from normal cells and can be exploited for development of anti-cancer therapeutics. Activation of the tumor specific M2 form of pyruvate kinase (PKM2) is a potential strategy for returning cancer cells to a metabolic state characteristic of normal cells. Here, we describe activators of PKM2 based upon a substituted thieno[3,2-b]pyrrole[3,2-d]pyridazinone scaffold. The synthesis of these agents, structure-activity relationships, analysis of activity at related targets (PKM1, PKR and PKL) and examination of aqueous solubility are investigated. These agents represent the second reported chemotype for activation of PKM2. Published by Elsevier Ltd.
• THIENO[3,2-B] PYRROLE[3,2-D]PYRIDAZINONE DERIVATIVES AND THEIR USE AS PKM2 DERIVATIVES FOR THE TREATMENT OF CANCER, OBESITY AND DIABETES RELATED DISORDERS
  申请人：Agios Pharmaceuticals, Inc.

  公开号：EP3924056A1

  公开（公告）日：2021-12-22
• [EN] THIENO[3,2-B] PYRROLE[3,2-D]PYRIDAZINONE DERIVATIVES AND THEIR USE AS PKM2 DERIVATIVES FOR THE TREATMENT OF CANCER, OBESITY AND DIABETES RELATED DISORDERS<br/>[FR] DÉRIVÉS THIÉNO[3,2-B]-PYRROLE[3,2-D]PYRIDAZINONES ET LEUR UTILISATION COMME DÉRIVÉS DE PKM2 POUR LE TRAITEMENT DE TROUBLES ASSOCIÉS AU CANCER, À L'OBÉSITÉ ET AU DIABÈTE
  申请人：AGIOS PHARMACEUTICALS INC

  公开号：WO2020167976A1

  公开（公告）日：2020-08-20

  Described herein are compounds that regulate pyruvate kinase activity, pharmaceutical compositions and methods of use thereof. These compounds are represented by Formula (I) wherein R2, L1-L2, U1-U7, m, ring A, and Q are as defined herein.