(R)-1,1-dioxo-isothiazolidine-3-carboxylic acid tert-butyl ester | 409107-74-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-1,1-dioxo-isothiazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (3R)-1,1-dioxo-1,2-thiazolidine-3-carboxylate
• CAS: 409107-74-0
• 化学式: C₈H₁₅NO₄S
• 分子量: 221.277
• InChiKey: JFUBUVMYQZXKSS-ZCFIWIBFSA-N

物化性质

• 沸点：
  313.5±52.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-溴甲基联苯 、 (R)-1,1-dioxo-isothiazolidine-3-carboxylic acid tert-butyl ester 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以80%的产率得到2(R)-2-biphenyl-4-ylmethyl-1,1-dioxo-λ⁶-isothiazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Sultam Hydroxamates as Novel Matrix Metalloproteinase Inhibitors

  摘要：

  In this communication we describe the design, synthesis, and evaluation of novel sultam hydroxamates 4 as MMP-2, -9, and -13 inhibitors. Compound 26 was found to be an active inhibitor (NIMP-2 IC50 = 1 nM) with 1000-fold selectivity over MMP-1 and good oral bioavailability (F = 43%) in mouse. An X-ray crystal structure of 26 in MMP-13 confirms the key hydrogen bonds and prime side binding in the active site.

  DOI：

  10.1021/jm049833g
• 作为产物：
  描述：

  丁氧基羰基-D-5-溴尿嘧啶 在 N-甲基吗啉 、 偶氮二甲酸二异丙酯 、 水 、 sodium acetate 、 氯 、 溶剂黄146 、 三苯基膦 、 三氟乙酸 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 (R)-1,1-dioxo-isothiazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  N-substituted sultam carboxylic acids as novel glycogen synthase activators

  摘要：

  我们发现了一类新型的N取代磺酰胺羧酸，具有细胞活性和口服生物利用度，作为强效的糖原合成酶激活剂。

  DOI：

  10.1039/c3md00053b

文献信息

• NOVEL CARBOXYLIC ACID ANALOGS AS GLYCOGEN SYNTHASE ACTIVATORS
  申请人：Bolin David Robert

  公开号：US20110136792A1

  公开（公告）日：2011-06-09

  Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of metabolic diseases and disorders such as, for example, type II diabetes mellitus.

  本文提供的化合物的化学式为(I)，以及其药用盐，其中取代基如规范中所披露。这些化合物及含有它们的药物组合物对于治疗代谢性疾病和紊乱，如二型糖尿病等，具有用处。
• [EN] CARBOXYLIC ACID ANALOGS AS GLYCOGEN SYNTHASE ACTIVATORS<br/>[FR] ANALOGUES D'ACIDES CARBOXYLIQUES COMME ACTIVATEURS DE LA GLYCOGÈNE SYNTHASE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2011067266A1

  公开（公告）日：2011-06-09

  Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of metabolic diseases and disorders such as, for example, type II diabetes mellitus.
• <i>N</i>-substituted sultam carboxylic acids as novel glycogen synthase activators
  作者：Yimin Qian、David R. Bolin、Karin Conde-Knape、Paul Gillespie、Stuart Hayden、Kuo-Sen Huang、Mei Liu、Andrée R. Olivier、Yonglin Ren、Joseph Sergi、Qing Xiang、Lin Yi、Weiya Yun、Xiaolei Zhang

  DOI：10.1039/c3md00053b

  日期：——

  We discovered a novel class ofN-substituted sultam carboxylic acids as potent glycogen synthase activators with cellular activity and oral bioavailability.

  我们发现了一类新型的N取代磺酰胺羧酸，具有细胞活性和口服生物利用度，作为强效的糖原合成酶激活剂。
• Sultam Hydroxamates as Novel Matrix Metalloproteinase Inhibitors
  作者：Robert J. Cherney、Ruowei Mo、Dayton T. Meyer、Karl D. Hardman、Rui-Qin Liu、Maryanne B. Covington、Mingxin Qian、Zelda R. Wasserman、David D. Christ、James M. Trzaskos、Robert C. Newton、Carl P. Decicco

  DOI：10.1021/jm049833g

  日期：2004.6.1

  In this communication we describe the design, synthesis, and evaluation of novel sultam hydroxamates 4 as MMP-2, -9, and -13 inhibitors. Compound 26 was found to be an active inhibitor (NIMP-2 IC50 = 1 nM) with 1000-fold selectivity over MMP-1 and good oral bioavailability (F = 43%) in mouse. An X-ray crystal structure of 26 in MMP-13 confirms the key hydrogen bonds and prime side binding in the active site.