N-t-butoxycarbonyl-3,5-dimethyl-L-tyrosine methyl ester | 579525-48-7

• 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-t-butoxycarbonyl-3,5-dimethyl-L-tyrosine methyl ester
• 英文别名: methyl (2S)-3-(4-hydroxy-3,5-dimethylphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 579525-48-7
• 化学式: C₁₇H₂₅NO₅
• 分子量: 323.389
• InChiKey: OZVIZRISVSEJAH-ZDUSSCGKSA-N

物化性质

• 沸点：
  473.3±45.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-chloromethyl-2-phenylbenzoxazole 、 N-t-butoxycarbonyl-3,5-dimethyl-L-tyrosine methyl ester 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以70%的产率得到N-t-butoxycarbonyl-3,5-dimethyl-O-[(2-phenyl)benzoxazol-7-yl]methyl-L-tyrosine methyl ester
  参考文献：
  名称：

  AROMATIC AMINO ACID DERIVATIVES AND MEDICINAL COMPOSITIONS

  摘要：

  公开号：

  EP1481965B1
• 作为产物：
  描述：

  (2S)-(N-tert-butoxycarbonylamino)-3-(2'-benzyloxy-1',3'-dimethylphen-5'-yl)-propionic acid methyl ester 在 1% Pd/C 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以85%的产率得到N-t-butoxycarbonyl-3,5-dimethyl-L-tyrosine methyl ester
  参考文献：
  名称：

  用于探测肽和蛋白质中质子耦合电子转移过程的酪氨酸类似物

  摘要：

  已经制备并表征了一系列类似于酪氨酸但在芳醇侧链的物理化学性质上不同的氨基酸。这些化合物有望用于理解肽和蛋白质中长程质子耦合电子转移过程中的结构、热力学和动力学之间的关系。通过用苯酚代替吡啶醇和嘧啶醇部分，可以诱导酪氨酸侧链的酸度、氧化还原电位和 OH 键强度的系统变化。通过在酚羟基邻位引入甲基和叔丁基取代基，可以进一步调节。非天然氨基酸是通过 Pd 催化交叉偶联制备的，相应的卤代芳醇被保护为苄基醚，与衍生自 N-Boc L-丝氨酸羧甲基酯的有机锌试剂交叉偶联。随后通过催化氢化的脱苄基以良好的产率得到酪氨酸类似物。分光光度法滴定显示约酪氨酸 pK(a) 减少。每个包含的氮原子 1.5 log 单位，以及 ca 的氧化（峰值）电位相应增加。分别为 200 mV。总而言之，这里描述的六种新氨基酸具有酚样侧链，其 pK(a) 的范围为 7.0 到大于 10，氧化（峰值）电位范围在 600 mV 左右生理pH值。进行自由基平衡

  DOI：

  10.1021/ja907921w

文献信息

• Aromatic amino acid derivates and medicinal compositions
  申请人：Endo Hitoshi

  公开号：US20050119256A1

  公开（公告）日：2005-06-02

  1. An aromatic amino acid derivative represented by the formula (I) or its pharmacologically acceptable salt: wherein, R 1 is a hydrogen atom or an amino-protecting group, R 2 is a halogen atom or an alkyl, aralkyl or aryl group, R 3 is circle over (1)} a hydrogen atom, circle over (2)} an aroylamino group, circle over (3)} a phenyl group substituted with lower alkyl, phenyl, phenoxy, etc. circle over (4)} a naphthyl or tetrahydronaphthyl group optionally substituted with hydroxy, lower alkoxy or di(lower)alkylamino, circle over (5)} an unsaturated mono-cyclic heterocyclic group containing N, O and/or S substituted with lower alkyl, phenyl, naphthyl or tetrahydroquinolyl, circle over (6)} an unsaturated or partially saturated condensed heterocyclic group containing N, O and/or S, optionally substituted with oxo, carboxy, amino, lower alkyl, etc.; X is a halogen atom, an alkyl group or an alkoxy group; Y is oxygen atom or nitrogen atom; I is 0 or 1; m is 0, 1 or 2; n is an integer of 0-5. This compound can inhibit a transporter (LAT1) of essential amino acid which is one of main nutrition for cancer cells and accordingly cause drain of the essential amino acid on the cancer cells and finally can prohibit the multiplication of cancer cells.

  一种芳香族氨基酸衍生物，其化学式为（I）或其药理学上可接受的盐：其中，R1为氢原子或氨基保护基；R2为卤素原子或烷基、芳基烷基或芳基基团；R3为circle over (1)}氢原子，circle over (2)}芳基氨基基团，circle over (3)}苯基，其取代基为较低的烷基、苯基、苯氧基等，circle over (4)}萘基或四氢萘基，可选地取代羟基、较低的烷氧基或二（较低）烷基氨基，circle over (5)}含N、O和/或S的不饱和单环杂环基团，取代基为较低的烷基、苯基、萘基或四氢喹啉基团，circle over (6)}含N、O和/或S的不饱和或部分饱和的紧缩杂环基团，可选地取代为氧代、羧基、氨基、较低的烷基等；X为卤素原子、烷基或烷氧基；Y为氧原子或氮原子；I为0或1；m为0、1或2；n为0-5的整数。该化合物可以抑制癌细胞的主要营养物质之一的必需氨基酸转运体（LAT1），从而导致癌细胞必需氨基酸的流失，最终可以抑制癌细胞的增殖。
• Aromatic amino acid derivatives and medicinal compositions
  申请人：——

  公开号：US07345068B2

  公开（公告）日：2008-03-18

  1. An aromatic amino acid derivative represented by the formula (I) or its pharmacologically acceptable salt: wherein, R1 is a hydrogen atom or an amino-protecting group, R2 is a halogen atom or an alkyl, aralkyl or aryl group, R3 is circle around (1)} a hydrogen atom, circle around (2)} an aroylamino group, circle around (3)} a phenyl group substituted with lower alkyl, phenyl, phenoxy, etc. circle around (4)} a naphthyl or tetrahydronaphthyl group optionally substituted with hydroxy, lower alkoxy or di(lower)alkylamino, circle around (5)} an unsaturated mono-cyclic heterocyclic group containing N, O and/or S substituted with lower alkyl, phenyl, naphthyl or tetrahydroquinolyl, circle around (6)} an unsaturated or partially saturated condensed heterocyclic group containing N, O and/or S, optionally substituted with oxo, carboxy, amino, lower alkyl, etc.; X is a halogen atom, an alkyl group or an alkoxy group; Y is oxygen atom or nitrogen atom; l is 0 or 1; m is 0, 1 or 2; n is an integer of 0-5. This compound can inhibit a transporter (LAT1) of essential amino acid which is one of main nutrition for cancer cells and accordingly cause drain of the essential amino acid on the cancer cells and finally can prohibit the multiplication of cancer cells.

  一种芳香族氨基酸衍生物，其化学式为（I）或其药学上可接受的盐：其中，R1是氢原子或氨基保护基，R2是卤素原子或烷基、芳基烷基或芳基基团，R3是圆圈1}氢原子，圆圈2}芳酰氨基基团，圆圈3}苯基取代较低烷基、苯基、苯氧基等的基团，圆圈4}萘基或四氢萘基基团，可选地取代羟基、较低烷氧基或二（较低）烷基氨基，圆圈5}含有N、O和/或S的不饱和单环杂环基团，取代较低烷基、苯基、萘基或四氢喹啉基团，圆圈6}含有N、O和/或S的不饱和或部分饱和的紧缩杂环基团，可选地取代氧代、羧基、氨基、较低烷基等；X是卤素原子、烷基或烷氧基；Y是氧原子或氮原子；l为0或1；m为0、1或2；n为0-5的整数。该化合物可以抑制癌细胞的主要营养物质之一的必需氨基酸的转运体（LAT1），从而导致癌细胞中必需氨基酸的流失，最终可以抑制癌细胞的增殖。
• Anticancer agent composition
  申请人：J-Pharma Co., Ltd.

  公开号：US10172835B2

  公开（公告）日：2019-01-08

  A method for treating cancer includes administering to a subject in need of the treatment an anticancer agent composition that includes the following agents as active ingredients; a LAT1 inhibitor, and one or more agents selected from the group consisting of an alkylating agent, a platinum-based antineoplastic agent, an anti-metabolite, a topoisomerase inhibitor, an anti-microtubule polymerizing agent, a hormonal agent, an anti-microtubule depolymerizing agent, an anticancer antibiotic, and a molecular targeted agent.

  一种治疗癌症的方法包括向需要治疗的受试者施用抗癌剂组合物，该组合物包括作为活性成分的下列制剂；LAT1抑制剂，以及选自以下组别的一种或多种制剂：烷化剂、铂类抗肿瘤剂、抗代谢剂、拓扑异构酶抑制剂、抗微管聚合剂、激素制剂、抗微管解聚剂、抗癌抗生素和分子靶向制剂。
• ANTI-MALIGNANT TUMOR AGENT COMPOSITION
  申请人：J-Pharma Co., Ltd.

  公开号：EP2959918B1

  公开（公告）日：2019-05-22
• AN ANTICANCER AGENT COMPOSITION
  申请人：J-PHARMA CO., LTD.

  公开号：US20160279103A1

  公开（公告）日：2016-09-29

  A method for treating cancer includes administering to a subject in need of the treatment an anticancer agent composition that includes the following agents as active ingredients; a LAT1 inhibitor, and one or more agents selected from the group consisting of an alkylating agent, a platinum-based antineoplastic agent, an anti-metabolite, a topoisomerase inhibitor, an anti-microtubule polymerizing agent, a hormonal agent, an anti-microtubule depolymerizing agent, an anticancer antibiotic, and a molecular targeted agent.