N-Boc-(S)-α-bromomethylalanine | 1073487-40-7

• 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-Boc-(S)-α-bromomethylalanine
• 英文别名: (2S)-3-bromo-2-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 1073487-40-7
• 化学式: C₉H₁₆BrNO₄
• 分子量: 282.134
• InChiKey: CYWQNOGUFFPCET-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-Boc-3-amino-3-methyl-2-oxetanone 在 magnesium bromide 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到N-Boc-(S)-α-bromomethylalanine
  参考文献：
  名称：

  A convenient transformation of α-alkylserines into α-halogenomethyl-α-alkylglycines

  摘要：

  An efficient and facile synthesis of N-Boc-alpha-chloromethyl- and alpha-bromomethyl-alpha-alkylglycines is reported that involves cyclization of N-Boc-alpha-alkylserines to the corresponding beta-lactones under Mitsunobu reaction conditions, followed by ring opening with anhydrous MgCl2 or MgBr2. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.08.098

文献信息

• OMEGA-AMINOALKYLAMIDES OF R-2-ARYL-PROPIONIC ACIDS AS INHIBITORS OF THE CHEMOTAXIS OF POLYMORPHONUCLEATE AND MONONUCLEATE CELLS
  申请人：ALLEGRETTI Marcello

  公开号：US20080045522A1

  公开（公告）日：2008-02-21

  (R)-2-Arylpropionamide compounds of formula (I) are described. The process for their preparation and pharmaceutical preparations thereof are also described. The 2-Arylpropionamides of the invention are useful in the prevention and treatment of tissue damage due to the exacerbate recruitment of polymorphonuclear leukocytes (leukocytes PMN) and of monocytes at the inflammatory sites. In particular, the invention relates to the R enantiomers of omega-aminoalkylamides of 2-aryl propionic acids, of formula (I), for use in the inhibition of the chemotaxis of neutrophils and monocytes induced by the C5a fraction of the complement and by other chemotactic proteins whose biological activity is associated with activation of a 7-TD receptor. Selected compounds of formula (I) are dual inhibitors of both the C5a-induced chemotaxis of neutrophils and monocytes and the IL-8-induced chemotaxis of PMN leukocytes. The compounds of the invention are used in the treatment of psoriasis, ulcerative cholitis, glomerular nephritis, acute respiratory insufficiency, idiopathic fibrosis, rheumatoid arthritis and in the prevention and the treatment of injury caused by ischemia and reperfusion.

  本文描述了公式(I)的(R)-2-芳基丙酰胺化合物，以及它们的制备过程和制药制剂。本发明中的2-芳基丙酰胺类化合物可用于预防和治疗由于在炎症部位诱导多形核白细胞（白细胞PMN）和单核细胞的加重招募而导致的组织损伤。特别是，本发明涉及公式(I)的ω-氨基烷基酰胺的R对映体，用于抑制由C5a补体分数和其他趋化蛋白诱导的中性粒细胞和单核细胞趋化，其生物活性与7-TD受体的激活有关。公式(I)的某些选择性化合物是同时抑制C5a诱导的中性粒细胞和单核细胞趋化以及IL-8诱导的PMN白细胞趋化的双重抑制剂。本发明中的化合物用于治疗牛皮癣、溃疡性结肠炎、肾小球肾炎、急性呼吸功能不全、特发性纤维化、类风湿关节炎以及预防和治疗缺血再灌注所致的损伤。
• A convenient transformation of α-alkylserines into α-halogenomethyl-α-alkylglycines
  作者：Adam Kudaj、Aleksandra Olma

  DOI：10.1016/j.tetlet.2008.08.098

  日期：2008.11

  An efficient and facile synthesis of N-Boc-alpha-chloromethyl- and alpha-bromomethyl-alpha-alkylglycines is reported that involves cyclization of N-Boc-alpha-alkylserines to the corresponding beta-lactones under Mitsunobu reaction conditions, followed by ring opening with anhydrous MgCl2 or MgBr2. (C) 2008 Elsevier Ltd. All rights reserved.