2-[2-(4-oxo-4-benzo[d][1,2,3]triazin-3-ylethyl)]-3-(4-pyrimidin-5-ylphenylthio) propionic acid | 427895-18-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-[2-(4-oxo-4-benzo[d][1,2,3]triazin-3-ylethyl)]-3-(4-pyrimidin-5-ylphenylthio) propionic acid
• 英文别名: 4-(4-Oxo-3,4-dihydro-1,2,3-benzotriazin-3-yl)-2-[4-(5-pyrimidyl)phenylsulphanylmethyl]butyric acid；4-(4-Oxo-1,2,3-benzotriazin-3-yl)-2-[(4-pyrimidin-5-ylphenyl)sulfanylmethyl]butanoic acid
• CAS: 427895-18-9
• 化学式: C₂₂H₁₉N₅O₃S
• 分子量: 433.491
• InChiKey: YCTUQENSYKMZFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[2-(4-oxo-4-benzo[d][1,2,3]triazin-3-ylethyl)]-3-(4-pyrimidin-5-ylphenylthio) propionic acid 在 bis-triphenylphosphine-palladium(II) chloride 三正丁基氢锡 、 1-羟基苯并三唑 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-hydroxy-2-[2-(4-oxo-4-benzo[d][1,2,3]triazin-3-ylethyl)]-3-(4-pyrimidin-5-ylphenylthio)-propionamide
  参考文献：
  名称：

  Solid-phase synthesis of α-substituted 3-bisarylthio N-Hydroxy propionamides as Specific MMP Inhibitors

  摘要：

  A novel series of potent and specific MMP-2,3,9,13 inhibitors has been obtained by modulation on solid phase by alpha and aryl substitutions on 3-arylthio-w-hydroxy-propionamides starting from itaconic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00311-x
• 作为产物：
  描述：

  tert-butyl-2-[2-(4-oxo-4H-benzo[d][1,2,3]-triazin-3-ylethyl)]-3-(4-pyrimidin-5-ylphenyltio) propionate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以77.5%的产率得到2-[2-(4-oxo-4-benzo[d][1,2,3]triazin-3-ylethyl)]-3-(4-pyrimidin-5-ylphenylthio) propionic acid
  参考文献：
  名称：

  Solid-phase synthesis of α-substituted 3-bisarylthio N-Hydroxy propionamides as Specific MMP Inhibitors

  摘要：

  A novel series of potent and specific MMP-2,3,9,13 inhibitors has been obtained by modulation on solid phase by alpha and aryl substitutions on 3-arylthio-w-hydroxy-propionamides starting from itaconic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00311-x

文献信息

• Carboxylic and hydroxamic acid compounds inhibiting metalloproteases, method for preparing same and pharmaceutical compositions containing them
  申请人：Les Laboratoires Servier

  公开号：US06605604B1

  公开（公告）日：2003-08-12

  The invention concerns a compound of formula (I) wherein: n is equal to 0 or 1; R1, R2, R3, R4 represent a hydrogen or an alkyl group, or R1 and R3 together form a cycloalkyl group; R5 represents a hydrogen, an alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, hetereoalkylalkyl, hetereocycloalkyl, hetereocycloalkylalkyl group (all optionally substituted), or a —CO—R6 group; and R6 represents R7 or OR7 or NR7R8, with R7 representing an aryl, arylalkyl, heteroaryl or heteroarylalkyl, heterocycloalkyl, heterocycloalkylalkyl group (all optionally substituted), and R8 representing an alkyl, aryl, arylalkyl, heteroaryl or heteroarylalkyl (all optionally substituted); or R5 and R6 form with the nitrogen atom and the Z group bearing them a saturated monocyclic, bicyclic or tricyclic group, partially unsaturated or unsaturated, with 5 to 16 chain links containing 1 to 7 heteroatoms and optionally substituted; R10 represents a hydrogen atom or a hydroxy group, and in the latter case R1, R2, R3, R4 are independently selected among hydrogen and alkyl; Z represents a hydroxy, alkoxy, alkenyloxy, benzyloxy group or a NH—OR group; X represents a sulphur, a SO, SO2 group (in those cases where R3 and R4 are different from an alkyl) or a group —CO—O— (in which case R1 and R3 form a cycloalkyl group), or X represents an oxygen atom; W represents a W1—(A)p or W1—B—W2—(A)p group wherein W1 and W2 represent an aryl or heteroaryl group, A is a standard substituent of aromatic cycles, B a bond, an oxygen or an alkylene, alkenylene, alkynylene group, and p is an integer ranging between 0 and 5; T1 and T2 represent a bond or an alkylene, alkenylene, or alkynylene group. The invention is useful for preparing medicines.

  该发明涉及一种具有以下结构的化合物（I）：其中：n等于0或1；R1、R2、R3、R4代表氢或烷基基团，或者R1和R3一起形成环烷基基团；R5代表氢、烷基、环烷基、环烷基烷基、芳基、芳基烷基、杂环芳基、杂环烷基烷基、杂环烷基、杂环烷基烷基基团（均可选择性取代），或—CO—R6基团；R6代表R7或OR7或NR7R8，其中R7代表芳基、芳基烷基、杂环芳基或杂环芳基烷基、杂环烷基、杂环烷基烷基基团（均可选择性取代），R8代表烷基、芳基、芳基烷基、杂环芳基或杂环芳基烷基（均可选择性取代）；或R5和R6与氮原子和携带它们的Z基团形成饱和的单环、双环或三环基团，部分不饱和或不饱和，含有1到7个杂原子和可选择性取代的5到16个链节；R10代表氢原子或羟基团，在后一种情况下，R1、R2、R3、R4独立地从氢和烷基中选择；Z代表羟基、烷氧基、烯基氧基、苄氧基或NH—OR基团；X代表硫、一个SO、SO2基团（在这些情况下R3和R4不同于烷基）或一个基团—CO—O—（在这种情况下R1和R3形成环烷基基团），或X代表一个氧原子；W代表W1—（A）p或W1—B—W2—（A）p基团，其中W1和W2代表芳基或杂环芳基，A是芳香环的标准取代基，B是键合、氧或烷基、烯基、炔基基团，p是介于0和5之间的整数；T1和T2代表键合或烷基、烯基或炔基基团。该发明用于制备药物。
• US6605604B1
  申请人：——

  公开号：US6605604B1

  公开（公告）日：2003-08-12
• Solid-phase synthesis of α-substituted 3-bisarylthio N-Hydroxy propionamides as Specific MMP Inhibitors
  作者：Anne-Marie Chollet、Thierry Le Diguarher、Nathalie Kucharczyk、Armelle Loynel、Marc Bertrand、Gordon Tucker、Nicolas Guilbaud、Mike Burbridge、Philippe Pastoureau、Armel Fradin、Massimo Sabatini、Jean-Luc Fauchère、Patrick Casara

  DOI：10.1016/s0968-0896(01)00311-x

  日期：2002.3

  A novel series of potent and specific MMP-2,3,9,13 inhibitors has been obtained by modulation on solid phase by alpha and aryl substitutions on 3-arylthio-w-hydroxy-propionamides starting from itaconic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.