pentafluorophenyl 1H-indole-5-carboxylate | 953029-90-8

• 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: pentafluorophenyl 1H-indole-5-carboxylate
• 英文别名: (2,3,4,5,6-pentafluorophenyl) 1H-indole-5-carboxylate
• CAS: 953029-90-8
• 化学式: C₁₅H₆F₅NO₂
• 分子量: 327.21
• InChiKey: LYEFRAXZUAZXBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  pentafluorophenyl 1H-indole-5-carboxylate 、 对氯苄胺 在 吡啶 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 N-(4-chlorobenzyl)-1H-indole-5-carboxamide
  参考文献：
  名称：

  Inhibitors of Src Homology-2 Domain Containing Protein Tyrosine Phosphatase-2 (Shp2) Based on Oxindole Scaffolds

  摘要：

  Screening of the NCl diversity set of compounds has led to the identification of 5 (NSC-117199), which inhibits the protein tyrosine phosphatase (PTP) Shp2 with an IC(50) of 47 mu M. A focused library incorporating an isatin scaffold was designed and evaluated for inhibition of Shp2 and Shp1 PTP activities. Several compounds were identified that selectively inhibit Shp2 over ShpI and PTP1B with low to submicromolar activity. A model for the binding of the active compounds is proposed.

  DOI：

  10.1021/jm8002526
• 作为产物：
  描述：

  吲哚-5-羧酸 、 三氟乙酸五氟苯酯 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以70%的产率得到pentafluorophenyl 1H-indole-5-carboxylate
  参考文献：
  名称：

  Inhibitors of Src Homology-2 Domain Containing Protein Tyrosine Phosphatase-2 (Shp2) Based on Oxindole Scaffolds

  摘要：

  Screening of the NCl diversity set of compounds has led to the identification of 5 (NSC-117199), which inhibits the protein tyrosine phosphatase (PTP) Shp2 with an IC(50) of 47 mu M. A focused library incorporating an isatin scaffold was designed and evaluated for inhibition of Shp2 and Shp1 PTP activities. Several compounds were identified that selectively inhibit Shp2 over ShpI and PTP1B with low to submicromolar activity. A model for the binding of the active compounds is proposed.

  DOI：

  10.1021/jm8002526

文献信息

• [EN] INDOLYLMETHYL-MORPHOLINE DERIVATIVES AS KINASE INHIBITORS<br/>[FR] DERIVES D'INDOLYLMETHYL-MORPHOLINE EN TANT QU'INHIBITEURS DES KINASES
  申请人：UCB PHARMA SA

  公开号：WO2010146351A1

  公开（公告）日：2010-12-23

  A series of morpholine derivatives, substituted in the 4-position by a substituted carbonyl or sulfonyl moiety, and in the 3-position by an optionally substituted indol-3-ylmethyl group, being selective inhibitors of PI3 kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.

  一系列在4-位置被取代的吗啉衍生物，通过取代的羰基或磺酰基团取代，并在3-位置通过一个可选择取代的吲哚-3-基甲基基团，作为选择性PI3激酶酶抑制剂，在医学上具有益处，例如在治疗炎症、自身免疫、心血管、神经退行性、代谢、肿瘤、疼痛或眼科疾病方面。
• [EN] SUBSTITUTED OXINDOLE DERIVATIVES AS PROTEIN TYROSINE KINASE AND AS PROTEIN SERINE/THREONINE KINASE INHIBITORS<br/>[FR] DERIVES SUBSTITUES D'OXINDOLE EN TANT QU'INHIBITEURS DE LA TYROSINE KINASE ET DE LA SERINE/THREONINE KINASE
  申请人：GLAXO GROUP LIMITED

  公开号：WO1999015500A1

  公开（公告）日：1999-04-01

  (EN) Compounds of formula (I): wherein X is N, CH, CCF3, or C(C1-12 aliphatic); R4 is sulfonic acid, C1-12 aliphatic-sulfonyl, sulfonyl-C1-12 aliphatic, C1-12 aliphatic-sulfonyl-C1-6 aliphatic, C1-6 aliphatic-amino, R7-sulfonyl, R7-sulfonyl -C1-12 aliphatic, R7-aminosulfonyl, R7-aminosulfonyl-C1-12 aliphatic, R7-sulfonylamino, R7-sulfonylamino-C1-12 aliphatic, aminosulfonylamino, di-C1-12 aliphatic amino, di-C1-12 aliphatic aminocarbonyl, di-C1-12 aliphatic aminosulfonyl, di-C1-12 aliphatic amino, di-C1-12 aliphatic aminocarbonyl, di-C1-12 aliphatic aminosulfonyl-C1-12 aliphatic, (R8)1-3-Arylamino, (R8)1-3-Arylsulfonyl, (R8)1-3-Aryl-aminosulfonyl, (R8)1-3-Aryl-sulfonylamino, Het-amino, Het-sulfonyl, Het-aminosulfonyl, aminoiminoamino, or aminoiminoaminosulfonyl, R5 is hydrogen; and further wherein R4 and R5 are optionally joined to form a fused ring, pharmaceutical formulations comprising them and their use in therapy, especially in the treatment of diseases mediated by CDK2 activity, such as alopecia induced by cancer chemotherapy or radiotherapy.(FR) L'invention concerne des composés représentés par la formule (I).X y est N, CH, CCF3, ou C(C1-12 aliphatique); R4 est acide sulfonique, C1-12 aliphatique sulfonyle, sulphonyle C1-12 aliphatique, C1-12 aliphatique sulfonyle-C1-16, aliphatique, C1-16 aliphatique-amino, R7-sulfonyle, R7-sulfonyle -C1-12 aliphatique, R7-aminosulfonyle, R7-aminosulfonyle-C1-12, aliphatique, R7-sulfonylamino, R7-sulfonylamino-C1-12 aliphatique, aminosulfonylamino, di-C1-12 aliphatique amino, di-C1-12 aliphatique aminocarbonyle, di-C1-12 aliphatique aminosulfonyle, di-C1-12 aliphatique amino, di-C1-12 aliphatique aminocarbonyle, di-C1-12 aliphatique aminosulfonyle C1-12 aliphatique, (R8)1-13-arylamino, (R8)1-13-arylsulfonyle, (R8)1-13-arylaminosulfonyle, (R8)1-13-arylsulfonylamino, het-amino, het-sulfonyle, het-aminosulfonyle, aminoiminoamino ou aminoiminoaminosulfonyle; R5 est hydrogène; en outre, R4 et R5 sont éventuellement réunis afin de former un cycle. L'invention concerne également des formulations pharmaceutiques qui renferment ces dérivés et leur utilisation thérapeutique, en particulier dans le traitement de maladies à médiation CDK2, telles que l'alopécie provoquée par la chimiothérapie ou la radiothérapie anticancéreuses.

  化合物的式子为(I)：其中X为N、CH、CCF3或C(C1-12脂肪基)；R4为磺酸、C1-12脂肪基磺酰、磺酰-C1-12脂肪基、C1-12脂肪基磺酰-C1-6脂肪基、C1-6脂肪基氨基、R7磺酰、R7磺酰-C1-12脂肪基、R7氨基磺酰、R7氨基磺酰-C1-12脂肪基、R7磺酰氨基、R7磺酰氨基-C1-12脂肪基、氨基磺酰氨基、双C1-12脂肪基氨基、双C1-12脂肪基氨基羰基、双C1-12脂肪基氨基磺酰、双C1-12脂肪基氨基、双C1-12脂肪基氨基羰基、双C1-12脂肪基氨基磺酰-C1-12脂肪基、(R8)1-3-芳基氨基、(R8)1-3-芳基磺酰、(R8)1-3-芳基氨基磺酰、(R8)1-3-芳基磺酰氨基、杂环氨基、杂环磺酰、杂环氨基磺酰、氨基亚氨基或氨基亚氨基磺酰；R5为氢；并且R4和R5可以选择性地连接形成融合环。其中药物制剂包括它们及其在治疗中的使用，特别是在CDK2活性介导的疾病治疗中，例如由癌症化疗或放疗引起的脱发。
• WO2007/117699
  申请人：——

  公开号：——

  公开（公告）日：——
• SUBSTITUTED OXINDOLE DERIVATIVES AS PROTEIN TYROSINE KINASE AND AS PROTEIN SERINE/THREONINE KINASE INHIBITORS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1009738A1

  公开（公告）日：2000-06-21
• Inhibitors of Src Homology-2 Domain Containing Protein Tyrosine Phosphatase-2 (Shp2) Based on Oxindole Scaffolds
  作者：Harshani R. Lawrence、Roberta Pireddu、Liwei Chen、Yunting Luo、Shen-Shu Sung、Ann Marie Szymanski、M. L. Richard Yip、Wayne C. Guida、Saïd M. Sebti、Jie Wu、Nicholas J. Lawrence

  DOI：10.1021/jm8002526

  日期：2008.8.1

  Screening of the NCl diversity set of compounds has led to the identification of 5 (NSC-117199), which inhibits the protein tyrosine phosphatase (PTP) Shp2 with an IC(50) of 47 mu M. A focused library incorporating an isatin scaffold was designed and evaluated for inhibition of Shp2 and Shp1 PTP activities. Several compounds were identified that selectively inhibit Shp2 over ShpI and PTP1B with low to submicromolar activity. A model for the binding of the active compounds is proposed.