N-[5-amino-2-diethylamino-pyrimidin-4-yl]-L-4-[dimethylaminocarbonyloxy]-phenylalanine tert-butyl ester | 630118-54-6

• 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: N-[5-amino-2-diethylamino-pyrimidin-4-yl]-L-4-[dimethylaminocarbonyloxy]-phenylalanine tert-butyl ester
• 英文别名: tert-butyl (2S)-2-[[5-amino-2-(diethylamino)pyrimidin-4-yl]amino]-3-[4-(dimethylcarbamoyloxy)phenyl]propanoate
• CAS: 630118-54-6
• 化学式: C₂₄H₃₆N₆O₄
• 分子量: 472.588
• InChiKey: NKRWLOLWAZFURH-IBGZPJMESA-N

物化性质

• 沸点：
  636.0±65.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-[5-amino-2-diethylamino-pyrimidin-4-yl]-L-4-[dimethylaminocarbonyloxy]-phenylalanine tert-butyl ester 在 吡啶 、 甲酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2S)-2-[[2-(diethylamino)-5-[methyl-(4-methylphenyl)sulfonylamino]pyrimidin-4-yl]amino]-3-[4-(dimethylcarbamoyloxy)phenyl]propanoic acid
  参考文献：
  名称：

  Arylsulfonamide pyrimidines as VLA-4 antagonists

  摘要：

  A series of (S)-2-(2-(diethylamino)-5-(N-alkyl-N-sulfonamido)pyrimidin-4-ylamino)-3-(4-(carbamoyloxy)phenyl)propanoic acid is discovered as orally available VLA-4 antagonists. Representative compounds 11b and 11p showed efficacy in multiple in vivo animal models. The in vitro selectivity of 11p is also described. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.010
• 作为产物：
  描述：

  L-酪氨酸叔丁酯 在 二乙基异丙基胺 、 palladium on activated charcoal 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 异丙醇 为溶剂， 生成 N-[5-amino-2-diethylamino-pyrimidin-4-yl]-L-4-[dimethylaminocarbonyloxy]-phenylalanine tert-butyl ester
  参考文献：
  名称：

  Arylsulfonamide pyrimidines as VLA-4 antagonists

  摘要：

  A series of (S)-2-(2-(diethylamino)-5-(N-alkyl-N-sulfonamido)pyrimidin-4-ylamino)-3-(4-(carbamoyloxy)phenyl)propanoic acid is discovered as orally available VLA-4 antagonists. Representative compounds 11b and 11p showed efficacy in multiple in vivo animal models. The in vitro selectivity of 11p is also described. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.010

文献信息

• WO2007/41324
  申请人：——

  公开号：——

  公开（公告）日：——
• CARBAMATE COMPOUNDS WHICH INHIBIT LEUKOCYTE ADHESION MEDIATED BY VLA-4
  申请人：Elan Pharmaceuticals Inc.

  公开号：EP1940827B1

  公开（公告）日：2011-03-16
• Carbamate compounds which inhibit leukocyte adhesion mediated by VLA-4
  申请人：Semko Michael Christopher

  公开号：US20070129390A1

  公开（公告）日：2007-06-07

  Disclosed are compounds which bind VLA-4. Certain of these compounds also inhibit leukocyte adhesion and, in particular, leukocyte adhesion mediated by VLA-4. Such compounds are useful in the treatment of inflammatory diseases in a mammalian patient, e.g., human, such as asthma, Alzheimer's disease, atherosclerosis, AIDS dementia, diabetes, inflammatory bowel disease, rheumatoid arthritis, tissue transplantation, tumor metastasis and myocardial ischemia. The compounds can also be administered for the treatment of inflammatory brain diseases such as multiple sclerosis.
• US7727996B2
  申请人：——

  公开号：US7727996B2

  公开（公告）日：2010-06-01
• US8158642B2
  申请人：——

  公开号：US8158642B2

  公开（公告）日：2012-04-17