(2S,4R)-[[1-(5-propylpyrimidin-2-yl)-4-tritylsulfanylpyrrolidin-2-yl]methyl]amine | 391889-56-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2S,4R)-[[1-(5-propylpyrimidin-2-yl)-4-tritylsulfanylpyrrolidin-2-yl]methyl]amine
• 英文别名: (2S,4R)-C-[1-(5-Propyl-pyrimidin-2-yl)-4-tritylsulfanyl-pyrrolidin-2-yl]-methylamine；[(2S,4R)-1-(5-propylpyrimidin-2-yl)-4-tritylsulfanylpyrrolidin-2-yl]methanamine
• CAS: 391889-56-8
• 化学式: C₃₁H₃₄N₄S
• 分子量: 494.704
• InChiKey: XYVZRBMRMUPTPP-URLMMPGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  80.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4R)-[[1-(5-propylpyrimidin-2-yl)-4-tritylsulfanylpyrrolidin-2-yl]methyl]amine 在 三乙基硅烷 、 sodium cyanoborohydride 、 三氟乙酸 、 zinc(II) chloride 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 (3R,5S)-5-[[(2,5-difluorophenyl)methylamino]methyl]-1-(5-propylpyrimidin-2-yl)pyrrolidine-3-thiol
  参考文献：
  名称：

  Endothelin-Converting Enzyme-1 Inhibition and Growth of Human Glioblastoma Cells

  摘要：

  Endothelin-1 (ET-1) is mitogenic and/or antiapoptotic in human cancers, and antagonists to ET-1 receptors are under evaluation for cancer treatment. Inhibition of ET-1 activation by the endothelin-converting enzymes 1(a-d) (ECE-1(a-d); EC 3.4.24.71) represents another approach to block the ET-1 effect in cancer. To evaluate this potential, we synthesized and characterized a series of low nanomolar nonpeptidic thiol-containing ECE-1 inhibitors, and evaluated their effect, as well as the effect of inhibitors for the related metalloproteases neprilysin (NEP; EC 3.4.24.11) and angiotensin-converting enzyme (ACE: EC 3.4.15.1). on human glioblastoma cell growth. Only ECE-1 inhibitors inhibited DNA synthesis by human glioblastoma cells. Exogenous addition of ET-1 or bigET-1 to glioblastoma cells did not counterbalance the growth inhibition elicited by ECE-1 inhibitors, suggesting that ECE-1 inhibitors block the proliferation of human glioblastoma cells most likely via a mechanism not involving extracellular production of ET-1. This class of molecules may thus represent novel therapeutic agents for the potential treatment of human cancer.

  DOI：

  10.1021/jm040857x
• 作为产物：
  描述：

  N-Boc-反式-4-羟基-L-脯氨酸甲酯 在 四氯化碳 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 一水合肼 、 N,N-二异丙基乙胺 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.91h， 生成 (2S,4R)-[[1-(5-propylpyrimidin-2-yl)-4-tritylsulfanylpyrrolidin-2-yl]methyl]amine
  参考文献：
  名称：

  Endothelin-Converting Enzyme-1 Inhibition and Growth of Human Glioblastoma Cells

  摘要：

  Endothelin-1 (ET-1) is mitogenic and/or antiapoptotic in human cancers, and antagonists to ET-1 receptors are under evaluation for cancer treatment. Inhibition of ET-1 activation by the endothelin-converting enzymes 1(a-d) (ECE-1(a-d); EC 3.4.24.71) represents another approach to block the ET-1 effect in cancer. To evaluate this potential, we synthesized and characterized a series of low nanomolar nonpeptidic thiol-containing ECE-1 inhibitors, and evaluated their effect, as well as the effect of inhibitors for the related metalloproteases neprilysin (NEP; EC 3.4.24.11) and angiotensin-converting enzyme (ACE: EC 3.4.15.1). on human glioblastoma cell growth. Only ECE-1 inhibitors inhibited DNA synthesis by human glioblastoma cells. Exogenous addition of ET-1 or bigET-1 to glioblastoma cells did not counterbalance the growth inhibition elicited by ECE-1 inhibitors, suggesting that ECE-1 inhibitors block the proliferation of human glioblastoma cells most likely via a mechanism not involving extracellular production of ET-1. This class of molecules may thus represent novel therapeutic agents for the potential treatment of human cancer.

  DOI：

  10.1021/jm040857x

文献信息

• Pyrrolidine derivatives
  申请人：——

  公开号：US20020055632A1

  公开（公告）日：2002-05-09

  The present invention relates to pyrrolidine derivatives useful as inhibitors of metalloproteases, e.g. zinc proteases, and which are effective in treating disease states associated with vasoconstriction.

  本发明涉及吡咯烷衍生物，可用作金属蛋白酶抑制剂，例如锌蛋白酶，并且对治疗与血管收缩相关的疾病状态有效。
• PYRIMIDINE DERIVATIVES
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1303507A1

  公开（公告）日：2003-04-23
• US6660738B2
  申请人：——

  公开号：US6660738B2

  公开（公告）日：2003-12-09
• [EN] PYRIMIDINE DERIVATIVES<br/>[FR] DERIVES DE PYRIMIDINE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2002006271A1

  公开（公告）日：2002-01-24

  The present invention relates to compounds of formula (I) wherein R?1, R2, R3, R4, X1, X2, X3, X4¿ and Y are as defined in the description and the claims and dimeric forms and/or pharmaceutically acceptable esters, and/or salts thereof. The compounds are useful as inhibitors of metalloproteases, e.g. zinc proteases, particularly zinc hydrolases, and which are effective in treating disease states are associated with vasoconstriction of increasing occurrences.