(喹啉-8-磺酰基氨基)乙酸 | 115241-94-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: (喹啉-8-磺酰基氨基)乙酸
• 英文名称: (quinolin-8-ylsulfonyl)glycine
• 英文别名: (quinoline-8-sulfonylamino)-acetic acid；(Quinoline-8-sulfonylamino)acetic acid；2-(quinolin-8-ylsulfonylamino)acetic acid
• CAS: 115241-94-6
• 化学式: C₁₁H₁₀N₂O₄S
• 分子量: 266.277
• InChiKey: SRSWCYQJDZNZEC-UHFFFAOYSA-N

物化性质

• 熔点：
  129 °C
• 沸点：
  537.3±56.0 °C(Predicted)
• 密度：
  1.491±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  (喹啉-8-磺酰基氨基)乙酸 在 caesium carbonate 、 三苯基二氯化膦 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 benzyl 2-(benzyloxy)-4-(N-(4-cyclohexylbenzyl)-2-(N-(prop-2-yn-1-yl)quinoline-8-sulfonamido)acetamido)benzoate
  参考文献：
  名称：

  Identification of Bidentate Salicylic Acid Inhibitors of PTP1B

  摘要：

  PTP1B is a master regulator in the insulin and leptin metabolic pathways. Hyper-activated PTP1B results in insulin resistance and is viewed as a key factor in the onset of type II diabetes and obesity. Moreover, inhibition of PTP1B expression in cancer cells dramatically inhibits cell growth in vitro and in vivo. Herein, we report the computationally guided optimization of a salicylic acid-based PTP1B inhibitor 6, identifying new and more potent bidentate PTP1B inhibitors, such as 20h, which exhibited a > 4-fold improvement in activity. In CHO-IR cells, 20f, 20h, and 20j suppressed PTP1B activity and restored insulin receptor phosphorylation levels. Notably, 20f, which displayed a 5-fold selectivity for PTP1B over the closely related PTP sigma protein, showed no inhibition of PTP-LAR, PRL2 A/S, MKPX, or papain. Finally, 20i and 20j displayed nanomolar inhibition of PTP sigma, representing interesting lead compounds for further investigation.

  DOI：

  10.1021/acsmedchemlett.5b00171
• 作为产物：
  描述：

  喹啉-8-磺酰氯 在 lithium hydroxide monohydrate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 (喹啉-8-磺酰基氨基)乙酸
  参考文献：
  名称：

  Identification of Bidentate Salicylic Acid Inhibitors of PTP1B

  摘要：

  PTP1B is a master regulator in the insulin and leptin metabolic pathways. Hyper-activated PTP1B results in insulin resistance and is viewed as a key factor in the onset of type II diabetes and obesity. Moreover, inhibition of PTP1B expression in cancer cells dramatically inhibits cell growth in vitro and in vivo. Herein, we report the computationally guided optimization of a salicylic acid-based PTP1B inhibitor 6, identifying new and more potent bidentate PTP1B inhibitors, such as 20h, which exhibited a > 4-fold improvement in activity. In CHO-IR cells, 20f, 20h, and 20j suppressed PTP1B activity and restored insulin receptor phosphorylation levels. Notably, 20f, which displayed a 5-fold selectivity for PTP1B over the closely related PTP sigma protein, showed no inhibition of PTP-LAR, PRL2 A/S, MKPX, or papain. Finally, 20i and 20j displayed nanomolar inhibition of PTP sigma, representing interesting lead compounds for further investigation.

  DOI：

  10.1021/acsmedchemlett.5b00171

文献信息

• Anthranilic acid derivatives and their use as activators of the hm74a receptor
  申请人：Campbell Matthew

  公开号：US20070191378A1

  公开（公告）日：2007-08-16

  Therapeutically active anthranilic acid derivatives of Formula (I), processes for the preparation of said derivatives, pharmaceutical formulations containing the compounds and the use of the compounds in therapy, particularly in the treatment of diseases in which under-activation of the HM74A receptor contributes to the disease or in which activation of the receptor will be beneficial, are disclosed.

  本文披露了公式（I）的治疗活性蒽酸衍生物，制备该衍生物的过程，含有该化合物的制药配方以及化合物在治疗中的使用，特别是在治疗HM74A受体欠活化导致疾病或激活该受体将有益的疾病中的使用。
• (<i>S</i>)-<i>N</i>-(2,5-Dimethylphenyl)-1-(quinoline-8-ylsulfonyl)pyrrolidine-2-carboxamide as a Small Molecule Inhibitor Probe for the Study of Respiratory Syncytial Virus Infection
  作者：Blake P. Moore、Dong Hoon Chung、Daljit S. Matharu、Jennifer E. Golden、Clinton Maddox、Lynn Rasmussen、James W. Noah、Melinda I. Sosa、Subramaniam Ananthan、Nichole, A. Tower、E. Lucile White、Fuli Jia、Thomas E. Prisinzano、Jeffrey Aubé、Colleen B. Jonsson、William E. Severson

  DOI：10.1021/jm300612z

  日期：2012.10.25

  A high-throughput, cell-based screen was used to identify chemotypes as inhibitors for human respiratory syncytial virus (hRSV). Optimization of a sulfonylpyrrolidine scaffold resulted in compound 50 that inhibited a virus-induced cytopathic effect in the entry stage of infection (EC50 = 2.3 +/- 0.8 mu M) with marginal cytotoxicity (CC50 = 30.9 +/- 1.1 mu M) and reduced viral titer by 100-fold. Compared to ribavirin, sulfonylpyrrolidine 50 demonstrated an improved in vitro potency and selectivity index.
• [EN] ANTHRANILIC ACID DERIVATIVES AND THEIR USE AS ACTIVATORS OF THE HM74A RECEPTOR<br/>[FR] COMPOSES CHIMIQUES
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2005016867A3

  公开（公告）日：2005-03-31
• BERNAT, ANDRE;DELEBASSEE, DENIS;FREHEL, DANIEL;MAFFRAND, JEAN-PIERRE;VALL+
  作者：BERNAT, ANDRE、DELEBASSEE, DENIS、FREHEL, DANIEL、MAFFRAND, JEAN-PIERRE、VALL+

  DOI：——

  日期：——
• ANTHRANILIC ACID DERIVATIVES AND THEIR USE AS ACTIVATORS OF THE HM74A RECEPTOR
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP1689699A2

  公开（公告）日：2006-08-16