N-formyl-3-methoxy-phenylalanine | 276874-38-5

• 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-formyl-3-methoxy-phenylalanine
• 英文别名: N-Formyl-3-methoxy-phenylalanin；2-Formamido-3-(3-methoxyphenyl)propanoic acid
• CAS: 276874-38-5
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: DOMXEETXCAPRNF-UHFFFAOYSA-N

物化性质

• 沸点：
  482.1±40.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-formyl-3-methoxy-phenylalanine 在 盐酸 、 氢氧化钾 、 palladium on activated charcoal 、 乙醇 作用下， 反应 8.0h， 生成 8-methoxyisoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Novel Cyclopropapyrroloindole Derivative (AT-3510) Bearing Methoxycarbonyl and Trifluoromethyl Groups

  摘要：

  The seco-Cl 3-methoxycarbonyl-2-trifluoromethylcyclopropapyrroloindole (MCTFCPI) derivatives dl- and/or (S)-10 carrying various acyl moieties at the NG-position were synthesized along with their prodrugs (S)-12, and their antitumor activity was evaluated. Among these derivatives, AT-3510 [(S)-12m], the novel prodrug MCTFCPI derivative carrying a 5-(7-methoxybenzofuran-2-ylcarbonyl)aminoindole-2-carbonyl group at the NG-position, was found to exhibit more excellent antitumor activity against human tumor xenografts than the clinical trial candidates carzelesin (6) and KW-2189 (7) and cisplatin.

  DOI：

  10.1021/jm980668c
• 作为产物：
  描述：

  N-benzoyl-3-methoxy-phenylalanine 在 盐酸 作用下， 生成 N-formyl-3-methoxy-phenylalanine
  参考文献：
  名称：

  29.小ber碱组的综合实验。第二部分 17-酮-3：12-二甲氧基-6：15：16：17-四氢小ber碱的合成

  摘要：

  DOI：

  10.1039/jr9380000172

文献信息

• Process for the preparation of optically active alpha-aminonitriles
  申请人：DSM N.V.

  公开号：EP1013773A1

  公开（公告）日：2000-06-28

  Process for the preparation of an α-aminonitrile with enhanced optical purity wherein a mixture of the enantiomers of a chiral N-formyl α-aminonitrile is brought into contact with an acylase, whereby one of the enantiomers of the N-formylaminonitrile is selectively deformylated into the unprotected corresponding α-aminonitrile, and a process for the preparation of an α-aminonitrile with enhanced optical purity wherein a mixture of the enantiomers of a chiral (unprotected) α-aminonitrile is subjected to a formylation reaction in the presence of an acylase and a formylating agent whereby one of the enantiomers is selectively converted in N-formyl α-aminonitrile. Preferably a peptide deformylase with a bivalent metal ion wherein the metal is chosen from group 5-11 of the periodic system, is used as acylase, for instance a peptide deformylase chosen from the class EC 3.5.2.27 or EC 3.5.1.31. Such peptide deformylases often contain the sequences of (I) HEXXH, (ii) EGCLS and (iii) GXGXAAXQ. The bivalent metal is preferably chosen from the group of Fe, Ni, Mn and Co, in particular Ni or Fe.

  制备光学纯度更高的α-氨基腈的工艺，其中将手性 N-甲酰基α-氨基腈的对映体混合物与酰化酶接触，从而使 N-甲酰基氨基腈的对映体之一选择性地变形为未受保护的相应α-氨基腈、以及制备光学纯度更高的α-氨基腈的工艺，其中手性（未受保护）α-氨基腈的对映体混合物在酰化酶和甲酰化剂存在下进行甲酰化反应，其中一种对映体选择性地转化为 N-甲酰基α-氨基腈。优选使用带有二价金属离子的肽变形酶作为酰化酶，其中金属离子选自周期系的第 5-11 组，例如选自 EC 3.5.2.27 或 EC 3.5.1.31 类的肽变形酶。这类肽变形酶通常含有 (I) HEXXH、(ii) EGCLS 和 (iii) GXGXAAXQ 的序列。 二价金属最好选自 Fe、Ni、Mn 和 Co 组，特别是 Ni 或 Fe。
• 118. The constitution of yohimbine and related alkaloids. Part VI. The synthesis of 1 : 2 : 3 : 4 : 6 : 7 : 12 : 12b-octahydro-2-ketoindolo-(2 : 3-a)pyridocoline and 1 : 2 : 3 : 4-tetrahydroindolo(2 : 3-a)pyridocoline
  作者：L. H. Groves、G. A. Swan

  DOI：10.1039/jr9520000650

  日期：——
• PROCESS FOR THE ENZYMATIC PREPARATION OF AMINO ACID DERIVATIVES WITH ENHANCED OPTICAL PURITY
  申请人：DSM IP Assets B.V.

  公开号：EP1141333B1

  公开（公告）日：2006-06-14
• PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE ALPHA-AMINONITRILES
  申请人：DSM N.V.

  公开号：EP1141369B1

  公开（公告）日：2003-04-09
• Novel Cyclopropapyrroloindole Derivative (AT-3510) Bearing Methoxycarbonyl and Trifluoromethyl Groups
  作者：Yasumichi Fukuda、Hirosuke Furuta、Yoshie Kusama、Hiroyuki Ebisu、Yasuo Oomori、Shiro Terashima

  DOI：10.1021/jm980668c

  日期：1999.4.22

  The seco-Cl 3-methoxycarbonyl-2-trifluoromethylcyclopropapyrroloindole (MCTFCPI) derivatives dl- and/or (S)-10 carrying various acyl moieties at the NG-position were synthesized along with their prodrugs (S)-12, and their antitumor activity was evaluated. Among these derivatives, AT-3510 [(S)-12m], the novel prodrug MCTFCPI derivative carrying a 5-(7-methoxybenzofuran-2-ylcarbonyl)aminoindole-2-carbonyl group at the NG-position, was found to exhibit more excellent antitumor activity against human tumor xenografts than the clinical trial candidates carzelesin (6) and KW-2189 (7) and cisplatin.