(L)-N-Boc-N-甲基酪氨酸甲酯 | 112196-59-5

• 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
• 中文名称: (L)-N-Boc-N-甲基酪氨酸甲酯
• 英文名称: Boc-N-Me-Tyr-OCH3
• 英文别名: (L)-N-Boc-N-methyltyrosine methyl ester；methyl N-Boc-N-methyl-L-tyrosinate；methyl N-(tert-butoxycarbonyl)-N-methyl-L-tyrosinate；N-[(1,1-Dimethylethoxy)carbonyl]-N-methyl-L-tyrosine methyl ester；methyl (2S)-3-(4-hydroxyphenyl)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoate
• CAS: 112196-59-5
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: APKANZULCFLXFM-ZDUSSCGKSA-N

物化性质

• 熔点：
  109-110 °C
• 沸点：
  432.4±40.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (L)-N-Boc-N-甲基酪氨酸甲酯 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以78%的产率得到N-methyl-L-tyrosine methyl ester
  参考文献：
  名称：

  Studies on the total synthesis of bouvardin and deoxybouvardin: cyclic hexapeptide cyclization studies and preparation of key partial structures

  摘要：

  DOI：

  10.1021/jo00238a005
• 作为产物：
  描述：

  L-酪氨酸甲酯 在 咪唑 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.0h， 生成 (L)-N-Boc-N-甲基酪氨酸甲酯
  参考文献：
  名称：

  Studies on the total synthesis of bouvardin and deoxybouvardin: cyclic hexapeptide cyclization studies and preparation of key partial structures

  摘要：

  DOI：

  10.1021/jo00238a005

文献信息

• TYROSINE AMIDE DERIVATIVES AS RHO- KINASE INHIBITORS
  申请人：CHIESI FARMACEUTICI S.P.A.

  公开号：US20180215758A1

  公开（公告）日：2018-08-02

  Bicyclic dihydropyrimidine-carboxamide compounds of formula I described herein inhibit Rho Kinase and may be used for the treatment of many disorders associated with ROCK enzymes mechanisms, such as pulmonary diseases including asthma, chronic obstructive pulmonary disease (COPD), idiopathic pulmonary fibrosis (IPF) and pulmonary arterial hypertension (PAH).

  本文描述的式I的双环二氢嘧啶羧酰胺化合物抑制Rho激酶，可用于治疗与ROCK酶机制相关的许多疾病，如包括哮喘、慢性阻塞性肺疾病（COPD）、特发性肺纤维化（IPF）和肺动脉高压（PAH）在内的肺部疾病。
• Regioselective Synthesis of 14-Membered Biaryl Ethers: Total Synthesis of RA-VII and Deoxybouvardin.
  作者：Tsutomu INOUE、Takashi INABA、Isao UMEZAWA、Masayuki YUASA、Hideji ITOKAWA、Katsuyuki OGURA、Katsuichiro KOMATSU、Hiroshi HARA、Osamu HOSHINO

  DOI：10.1248/cpb.43.1325

  日期：——

  In order to obtain a key compound (22a") for synthesis of RA-VII (1) and deoxybouvardin (2), construction of the 14-membered ring system was performed by means of thallium trinitrate-mediated oxidation of the tetrahalogeno amides 5-7. The dibromo dichloro amide 6 or the bromo trichloro amide 7 gave a natural type of 14-membered ring dienone (23a or 23c), whereas the tetrabromo amide 5 gave an unnatural type of product, 19a. The formation of the latter product 19a could be understood on the basis of energy calculations on plausible intermediates 26a-c and 27a-c in the transition state in the oxidaive coupling reaction. Compound 23a was further converted to 22a" through conventional procedures (aromatization; methylation; catalytic hydrogenation). This intermediate was readily converted to 1 and 2. Thus, total synthesis of RA-VII (1) and deoxybouvardin (2) was achieved for the first time.

  为了获得合成RA-VII（1）和去氧布瓦丁（2）的关键化合物（22a"），通过三硝酸铋介导的氧化反应对四卤酰胺5-7构建了14元环体系。二溴二氯酰胺6或溴三氯酰胺7产生了一种天然类型的14元环二烯酮（23a或23c），而四溴酰胺5则产生了一种非自然的产物19a。产物19a的形成可以通过对氧化偶联反应中可能的过渡态中间体26a-c和27a-c进行能量计算来理解。化合物23a通过常规程序（芳构化；甲基化；催化氢化）进一步转化为22a"。该中间体可以很方便地转化为1和2。因此，RA-VII（1）和去氧布瓦丁（2）的总合成首次得以实现。
• Tyrosine amide derivatives as Rho-Kinase inhibitors
  申请人：CHIESI FARMACEUTICI S.P.A.

  公开号：US10954236B2

  公开（公告）日：2021-03-23

  Bicyclic dihydropyrimidine-carboxamide compounds of formula I described herein inhibit Rho Kinase and may be used for the treatment of many disorders associated with ROCK enzymes mechanisms, such as pulmonary diseases including asthma, chronic obstructive pulmonary disease (COPD), idiopathic pulmonary fibrosis (IPF) and pulmonary arterial hypertension (PAH).

  本文所述式 I 的双环二氢嘧啶甲酰胺化合物可抑制 Rho 激酶，并可用于治疗与 ROCK 酶机制相关的多种疾病，如肺部疾病，包括哮喘、慢性阻塞性肺病 (COPD)、特发性肺纤维化 (IPF) 和肺动脉高压 (PAH)。
• Mild Ullmann-Type Biaryl Ether Formation Reaction by Combination ofortho-Substituent and Ligand Effects
  作者：Qian Cai、Benli Zou、Dawei Ma

  DOI：10.1002/anie.200503538

  日期：2006.2.13
• Synthesis, radiolabeling, and preliminary biological evaluation of [3H]-1-[(S)-N,O-bis-(isoquinolinesulfonyl)-N-methyl-tyrosyl]-4-(o-tolyl)-piperazine, a potent antagonist radioligand for the P2X7 receptor
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Maria Giovanna Pavani、Mojgan Aghazadeh Tabrizi、Allan R. Moorman、Francesco Di Virgilio、Elena Cattabriga、Cecilia Pancaldi、Stefania Gessi、Pier Andrea Borea

  DOI：10.1016/j.bmcl.2004.07.095

  日期：2004.11

  The design, synthesis, and preliminary biological evaluation of the first potent radioligand antagonist for the P2X(7) receptor, named [H-3]-1-[(S)-N,O-bis-(isoquinolinesulfonyl)-N-methyl-tyrosyl]-4-(o-tolyl)-piperazine (compound 13), are reported. This compound bound to human P2X(7) receptors expressed in HEK transfected cells with K-D and B-max value of 3.46 +/- 0.1 nM and 727 +/- 73 fmol/mg of protein, respectively. The high affinity and facile labeling makes it a promising radioligand for a further characterization of P2X(7) receptor subtype. (C) 2004 Elsevier Ltd. All rights reserved.