methyl 3-hydroxy-2-(4-methoxybenzenesulfonylamino)propionate | 85622-74-8

• 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: methyl 3-hydroxy-2-(4-methoxybenzenesulfonylamino)propionate
• 英文别名: methyl N-((4-methoxyphenyl)sulfonyl)serinate；methyl 3-hydroxy-2-[(4-methoxyphenyl)sulfonylamino]propanoate
• CAS: 85622-74-8
• 化学式: C₁₁H₁₅NO₆S
• mdl: MFCD12643162
• 分子量: 289.309
• InChiKey: FAPDSMKBFFNYKA-UHFFFAOYSA-N

物化性质

• 熔点：
  92-94 °C
• 沸点：
  480.9±55.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-hydroxy-2-(4-methoxybenzenesulfonylamino)propionate 在 palladium on activated charcoal ammonium formate 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 2-[(2-Aminobenzyl)-(4-methoxybenzenesulfonyl)amino]-3-hydroxypropionate
  参考文献：
  名称：

  Benzodiazepine inhibitors of the MMPs and TACE

  摘要：

  A series of benzodiazepine inhibitors of the MMPs and TACE has been developed. These compounds display an interesting selectivity profile and should be useful tools for exploring the biological relevance of such selectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00633-9
• 作为产物：
  描述：

  对甲氧基苯磺酰氯 在 三乙胺 、 柠檬酸 作用下， 以 二氯甲烷 为溶剂， 以5.0 g (54%)的产率得到methyl 3-hydroxy-2-(4-methoxybenzenesulfonylamino)propionate
  参考文献：
  名称：

  Acetylenic &agr;-amino acid-based sulfonamide hydroxamic acid tace inhibitors

  摘要：

  该式化合物在治疗由TNF-α介导的疾病条件中很有用，如类风湿性关节炎、骨关节炎、败血症、艾滋病、溃疡性结肠炎、多发性硬化症、克罗恩病和软骨退行性损失。

  公开号：

  US06225311B1

文献信息

• Allenic aryl sulfonamide hydroxamic acids as matrix metalloproteinase and tace inhibitors
  申请人：American Cyanamid Company

  公开号：US20030130238A1

  公开（公告）日：2003-07-10

  Compounds of the formula 1 are useful in treating disease conditions mediated by TNF-&agr;, such as rheumatoid arthritis, osteoarthritis, sepsis, AIDS, ulcerative colitis, multiple sclerosis, Crohn's disease, degenerative cartilage loss, graft rejection, cachexia, inflammation, fever, insulin resistance, septic shock, congestive heart failure, inflammatory disease of the central nervous system, inflammatory bowel disease and HIV.

  式1的化合物在治疗由TNF-α介导的疾病条件中很有用，如类风湿性关节炎、骨关节炎、败血症、艾滋病、溃疡性结肠炎、多发性硬化症、克罗恩病、退行性软骨丧失、移植排斥、虚弱、炎症、发热、胰岛素抵抗、脓毒性休克、充血性心力衰竭、中枢神经系统炎症性疾病、炎症性肠病和艾滋病。
• Asymmetric Synthesis of β ² ‐Aryl Amino Acids through Pd‐Catalyzed Enantiospecific and Regioselective Ring‐Opening Suzuki–Miyaura Arylation of Aziridine‐2‐carboxylates
  作者：Youhei Takeda、Tetsuya Matsuno、Akhilesh K. Sharma、W. M. C. Sameera、Satoshi Minakata

  DOI：10.1002/chem.201902009

  日期：2019.8

  A Pd‐catalyzed enantiospecific and regioselective ring‐opening Suzuki–Miyaura arylation of aziridine‐2‐carboxylates was developed. The cross‐coupling allows for the asymmetric preparation of enantioenriched β2‐aryl amino acids, starting from commercially available enantiopure d‐ and l‐serine esters. The mechanism and selectivity of the reaction was rationalized based on computational models.

  开发了钯催化的对映体特异性和区域选择性开环的Aziridine-2-羧酸盐的Suzuki-Miyaura芳基化反应。交叉耦合允许对映体富集的β不对称制备2 -芳基氨基酸，从可商购的对映体纯起始d -和升-丝氨酸酯。基于计算模型对反应的机理和选择性进行了合理化。
• 2,3,4,5-tetrahydro-1H-(1,4)benzodiazepine-3-hydroxamic acids
  申请人：American Cyanamid Company

  公开号：US06544984B1

  公开（公告）日：2003-04-08

  Compounds having the following formula:   are useful in treating disease conditions mediated by matrix metalloproteinases and TACE, such as tumor growth, osteoarthritis, rheumatoid arthritis and degenerative cartilage loss.

  具有以下化学式的化合物在治疗由基质金属蛋白酶和TACE介导的疾病条件中很有用，例如肿瘤生长、骨关节炎、类风湿性关节炎和软骨退行性损失。
• 2,3,4,5-tetrahydro-1H-[1,4]-benzodiazepine-3-hydroxyamic acids
  申请人：American Cyanamid Company

  公开号：US06071903A1

  公开（公告）日：2000-06-06

  Compounds are provided having the following formula: ##STR1## wherein R, R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are defined in the specification, which have matrix metalloproteinase inhibiting activity.

  提供具有以下公式的化合物：##STR1## 其中R、R.sub.1、R.sub.2、R.sub.3和R.sub.4在规范中有定义，并具有基质金属蛋白酶抑制活性。
• The synthesis and biological activity of a novel series of diazepine MMP inhibitors
  作者：Jeremy I. Levin、John F. DiJoseph、Loran M. Killar、Amy Sung、Thomas Walter、Michele A. Sharr、Catherine E. Roth、Jerauld S. Skotnicki、J.Donald Albright

  DOI：10.1016/s0960-894x(98)00473-9

  日期：1998.10

  A novel series of diazepine-based hydroxamic acid inhibitors of MMP-1, MMP-9, and MMP-13 were prepared and evaluated both in vitro and in vivo.

  制备了一系列新的基于二氮杂卓的MMP-1，MMP-9和MMP-13的异羟肟酸抑制剂，并在体内和体外进行了评估。