1-benzenesulfonyl-3-iodo-1H-pyrrolo[2,3-c]pyridine | 887115-55-1

• 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: 1-benzenesulfonyl-3-iodo-1H-pyrrolo[2,3-c]pyridine
• 英文别名: 3-iodo-1-benzenesulfonyl-6-azaindole；3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridine；1-(benzenesulfonyl)-3-iodopyrrolo[2,3-c]pyridine
• CAS: 887115-55-1
• 化学式: C₁₃H₉IN₂O₂S
• 分子量: 384.197
• InChiKey: KNWORKBAWASJSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzenesulfonyl-3-iodo-1H-pyrrolo[2,3-c]pyridine 在 四(三苯基膦)钯 、 sodium methylate 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 1.75h， 生成 4-(1H-pyrrolo[2,3-c]pyridin-3-yl)pyridin-2-amine
  参考文献：
  名称：

  Developing DYRK inhibitors derived from the meridianins as a means of increasing levels of NFAT in the nucleus

  摘要：

  A structure-activity relationship has been developed around the meridianin scaffold for inhibition of Dyrk1a. The compounds have been focussed on the inhibition of kinase Dyrk1a, as a means to retain the transcription factor NFAT in the nucleus. NFAT is responsible for up-regulation of genes responsible for the induction of a slow, oxidative skeletal muscle phenotype, which may be an effective treatment for diseases where exercise capacity is compromised. The SAR showed that while strong Dyrk1a binding was possible with the meridianin scaffold the compounds have no effect on NFAT localisation, however, by moving from the indole to a 6-azaindole scaffold both potent Dyrk1a binding and increased NFAT residence time in the nucleus were obtained - properties not observed with the reported Dyrk1a inhibitors. One compound was shown to be effective in an ex vivo muscle fiber assay. The increased biological activity is thought to arise from the added interaction between the azaindole nitrogen and the lysine residue in the back pocket. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.03.037
• 作为产物：
  描述：

  6-氮杂吲哚 在 N-碘代丁二酰亚胺 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 5.0h， 生成 1-benzenesulfonyl-3-iodo-1H-pyrrolo[2,3-c]pyridine
  参考文献：
  名称：

  Developing DYRK inhibitors derived from the meridianins as a means of increasing levels of NFAT in the nucleus

  摘要：

  A structure-activity relationship has been developed around the meridianin scaffold for inhibition of Dyrk1a. The compounds have been focussed on the inhibition of kinase Dyrk1a, as a means to retain the transcription factor NFAT in the nucleus. NFAT is responsible for up-regulation of genes responsible for the induction of a slow, oxidative skeletal muscle phenotype, which may be an effective treatment for diseases where exercise capacity is compromised. The SAR showed that while strong Dyrk1a binding was possible with the meridianin scaffold the compounds have no effect on NFAT localisation, however, by moving from the indole to a 6-azaindole scaffold both potent Dyrk1a binding and increased NFAT residence time in the nucleus were obtained - properties not observed with the reported Dyrk1a inhibitors. One compound was shown to be effective in an ex vivo muscle fiber assay. The increased biological activity is thought to arise from the added interaction between the azaindole nitrogen and the lysine residue in the back pocket. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.03.037

文献信息

• [EN] 2,4- DIARYL - SUBSTITUTED [1,8] NAPHTHYRIDINES AS KINASE INHIBITORS FOR USE AGAINST CANCER<br/>[FR] [1,8]-NAPHTYRIDINES SUBSTITUÉES PAR 2,4-DIARYLE EN TANT QU'INHIBITEURS DE KINASE, DESTINÉES À UNE UTILISATION CONTRE LE CANCER
  申请人：MERCK PATENT GMBH

  公开号：WO2012000595A1

  公开（公告）日：2012-01-05

  The present invention relates to novel [1,8]naphthyridine derivatives of formula (I) and to the use of such compounds in which the inhibition, regulation and/or modulation of signal transduction by ATP consuming proteins like kinases plays a role, particularly to inhibitors of TGF-beta receptor kinases, and to the use of such compounds for the treatment of kinase-induced diseases, in particular for the treatment of tumors.

  本发明涉及新型[1,8]萘啶衍生物的化学式(I)，以及利用这类化合物在ATP消耗蛋白质如激酶中抑制、调节和/或调制信号传导的用途，特别是TGF-beta受体激酶的抑制剂，以及利用这类化合物治疗激酶诱导的疾病，尤其是肿瘤的治疗。
• 2,4-DIARYL - SUBSTITUTED [1,8] NAPHTHYRIDINES AS KINASE INHIBITORS FOR USE AGAINST CANCER
  申请人：Dorsch Dieter

  公开号：US20130102603A1

  公开（公告）日：2013-04-25

  The present invention relates to novel [1,8]naphthyridine derivatives of formula (I) and to the use of such compounds in which the inhibition, regulation and/or modulation of signal transduction by ATP consuming proteins like kinases plays a role, particularly to inhibitors of TGF-beta receptor kinases, and to the use of such compounds for the treatment of kinase-induced diseases, in particular for the treatment of tumors.

  本发明涉及公式（I）的新型[1,8]萘啶衍生物，以及利用这些化合物在ATP消耗蛋白质如激酶中发挥作用的信号传导的抑制、调节和/或调控，特别是TGF-beta受体激酶的抑制剂，以及利用这些化合物治疗激酶诱导疾病，特别是治疗肿瘤的用途。
• 7-AZAINDOLE DERIVATIVES
  申请人：Dorsch Dieter

  公开号：US20130310391A1

  公开（公告）日：2013-11-21

  Compounds of the formula (I) in which R, R 1 , R 2 and R 3 have the meanings indicated in Claim 1 , are inhibitors of PDK1 and cell proliferation/cell vitality and can be employed for the treatment of tumours.

  式（I）中R、R1、R2和R3的化合物具有在权利要求1中指示的含义，可以抑制PDK1和细胞增殖/细胞活力，并可用于肿瘤的治疗。
• Tgf-Beta Inhibitors
  申请人：Diefenbacher Clive Gideon

  公开号：US20080262004A1

  公开（公告）日：2008-10-23

  The present invention is directed to inhibitors of TGF-β of Formula I:

  本发明涉及TGF-β的抑制剂，其化学式为I：
• TGF-β inhibitors
  申请人：Eli Lilly and Company

  公开号：US07511056B2

  公开（公告）日：2009-03-31

  The present invention is directed to inhibitors of TGF-β of Formula I:

  本发明涉及TGF-β的抑制剂，其化学式为I：