7C3Cvm6gpq | 1320360-90-4

• 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: 7C3Cvm6gpq
• 英文别名: 2-methylpropoxycarbonyl (2R)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 1320360-90-4
• 化学式: C₁₃H₂₃NO₇
• 分子量: 305.328
• InChiKey: LLLDEKZGYOZVDH-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(((3'-fluoro)benzyloxy)methyl)benzylamine 、 7C3Cvm6gpq 以 四氢呋喃 为溶剂， 以3.3 g的产率得到(R)-N-4'-(((3''-fluoro)benzyloxy)methyl)benzyl 2-N-(tert-butoxycarbonyl)amino-3-hydroxypropionamide
  参考文献：
  名称：

  Merging the Structural Motifs of Functionalized Amino Acids and α-Aminoamides: Compounds with Significant Anticonvulsant Activities

  摘要：

  Functional amino acids (FAAs) and alpha-aminoamides (AAAs) are two classes of antiepileptic drugs (AEDs) that exhibit pronounced anticonvulsant activities. We combined key structural pharmacophores present in FAAs and AAAs to generate a new series of compounds and document that select compounds exhibit activity superior to either the prototypical FAA (lacosamide) or the prototypical AAA (safinamide) in the maximal electroshock (MES) seizure model in rats. A representative compound, (R)-N-4'-((3 ''-fluoro)benzyloxy)benzyl 2-acetamido-3-methoxypropionamide ((R)-10), was tested in the MES (mice, ip), MES (rat, po), psychomotor 6 Hz (32 mA) (mice, ip), and hippocampal kindled (rat, ip) seizure tests providing excellent protection with ED50 values of 13, 14, similar to 10 mg/kg, and 12 mg/kg, respectively. In the rat sciatic nerve ligation model (ip), (R)-10 (12 mg/kg) provided an 11.2-fold attenuation of mechanical allodynia. In the mouse biphasic formalin pain model (ip), (R)-10 (15 mg/kg) reduced pain responses in the acute and the chronic inflammatory phases.

  DOI：

  10.1021/jm100185c
• 作为产物：
  描述：

  BOC-D-丝氨酸 、 氯甲酸异丁酯 在 N-甲基吗啉 作用下， 以 乙酸乙酯 为溶剂， 生成 7C3Cvm6gpq
  参考文献：
  名称：

  LACOSAMIDE INTERMEDIATE COMPOUND, PREPARATION METHOD THEREOF AND USE THEREOF

  摘要：

  提供了一种新的化合物，用于制备拉考酰胺。还提供了一种新颖的制备拉考酰胺的方法。在反应过程中，没有使用昂贵的碘甲烷和氧化银，也没有使用Pd-c催化剂，因此生产成本低，原材料和辅助材料廉价且易获得，工艺简单，易于实现工业化生产；此外，产率高，可以实现良好的经济效益。

  公开号：

  US20120283466A1

文献信息

• Preparation and opioid activity of analogs of the analgesic dipeptide 2,6-dimethyl-L-tyrosyl-N-(3-phenylpropyl)-D-alaninamide
  作者：Nizal S. Chandrakumar、Peter K. Yonan、Awilda Stapelfeld、Michael Savage、Elaine Rorbacher、Patricia C. Contreras、Donna Hammond

  DOI：10.1021/jm00080a005

  日期：1992.1

  A number of analogues of the recently disclosed analgesic dipeptide 2,6-dimethyl-L-tyrosyl-D-alanine-phenylpropylamide (SC-39566,2) were prepared. These analogues contained oxymethylene, aminomethylene, ketomethylene, bismethylene, and trans double bond (including vinyl fluoride) isosteric replacements for the amide bond between the D-alanine and phenylpropylamine units in 2. These compounds were tested in opioid binding assays and in the mouse writhing assay for analgesic activity. Though not as potent as 2, the oxymethylene, and trans double bond isosteres showed analgesic activity. The aminomethylene analogues also showed binding activity in subnanomolar concentrations at the mu-receptor. The amide bond between 2,6-dimethyl-L-tyrosine and D-alanine units seems to be critical for opioid activity.
• [EN] NOVEL N-BENZYLAMIDE SUBSTITUTED DERIVATIVES OF 2-(ACYLAMIDO)ACETIC ACID AND 2-(ACYLAMIDO)PROPIONIC ACIDS: POTENT NEUROLOGICAL AGENTS<br/>[FR] NOUVEAUX DÉRIVÉS SUBSTITUÉS PAR N-BENZYLAMIDE D'ACIDE 2-(ACYLAMIDO)ACÉTIQUES ET ACIDES 2-(ACYLAMIDO)PROPIONIQUES : AGENTS NEUROLOGIQUES PUISSANTS
  申请人：UNIV NORTH CAROLINA

  公开号：WO2009145816A3

  公开（公告）日：2010-02-25
• US8829226B2
  申请人：——

  公开号：US8829226B2

  公开（公告）日：2014-09-09