tert-butyl (2S)-4-bromo-2-(N-benzyloxycarbonyl)aminobutyrate | 601491-39-8

• 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: tert-butyl (2S)-4-bromo-2-(N-benzyloxycarbonyl)aminobutyrate
• 英文别名: (S)-2-benzyloxycarbonylamino-4-bromo-butyric acid tert-butyl ester；tert-butyl (2S)-2-{[(benzyloxy)carbonyl]amino}-4-bromobutanoate；tert-butyl (S)-2-{[(benzyloxy)carbonyl]amino}-4-bromo-butanoate；(S)-2-benzyloxycarbonylamino-4-bromo-butyric acid t-butyl ester；tert-butyl (2S)-4-bromo-2-(phenylmethoxycarbonylamino)butanoate
• CAS: 601491-39-8
• 化学式: C₁₆H₂₂BrNO₄
• 分子量: 372.259
• InChiKey: QMBVLZOEQAEXJC-ZDUSSCGKSA-N

物化性质

• 沸点：
  466.2±45.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-4-bromo-2-(N-benzyloxycarbonyl)aminobutyrate 在 [tetrabutylammonium]2[WSe4] 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以85%的产率得到Cbz-hSec(1)-OtBu.Cbz-hSec(1)-OtBu
  参考文献：
  名称：

  Utility of tetrathiomolybdate and tetraselenotungstate: efficient synthesis of cystine, selenocystine, and their higher homologues

  摘要：

  Efficient synthesis of cystine, selenocystine, and their higher homologues like homo and bishomo amino acid derivatives from natural amino acid derivatives using tetrathiomolybdate and tetraselenotungstate reagents under mild and neutral conditions is reported. The generality of the reaction has been studied by capping various groups to amino and carboxyl components of canonical amino acids. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01222-x
• 作为产物：
  描述：

  (S)-2-benzyloxycarbonylamino-succinic acid 1-tert-butyl ester 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 氯甲酸乙酯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 tert-butyl (2S)-4-bromo-2-(N-benzyloxycarbonyl)aminobutyrate
  参考文献：
  名称：

  WO2006/117552

  摘要：

  公开号：

文献信息

• PTERIDINE DERIVATIVES AS POLO-LIKE KINASE INHIBITORS USEFUL IN THE TREATMENT OF CANCER
  申请人：Moffat David Festus Charles

  公开号：US20100216802A1

  公开（公告）日：2010-08-26

  Compound of formula (I) are inhibitors of Polo-like kinases (PLKs), and are useful in treatment of cell proliferative diseases: wherein R 1 and R 2 are hydrogen, or an optionally substituted (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl or (C 3 -C 6 )cycloalkyl group; R 3 and R 3 ′ are independently selected from hydrogen, —CN, hydroxyl, halogen, optionally substituted (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl or (C 3 -C 6 )cycloalkyl, —NR 5 R 6 or C 1 -C 4 alkoxy, wherein R 5 and R 6 are independently hydrogen or optionally substituted (C 1 -C 6 )alkyl; ring A is an optionally substituted mono- or bi-cyclic carbocyclic or heterocyclic ring or a ring system having up to 12 ring atoms; T is a radical of formula R-L 1 -Y 1 — wherein R is an alpha amino acid or alpha amino acid ester motif, linked to ring A by linker R-L 1 -Y 1 — as defined in the claims.

  式(I)的化合物是Polo样激酶（PLKs）的抑制剂，可用于治疗细胞增殖性疾病：其中R1和R2是氢，或者是可选取代的（C1-C6）烷基，（C2-C6）烯基，（C2-C6）炔基或（C3-C6）环烷基；R3和R3'分别选自氢，—CN，羟基，卤素，可选取代的（C1-C6）烷基，（C2-C6）烯基，（C2-C6）炔基或（C3-C6）环烷基，—NR5R6或C1-C4烷氧基，其中R5和R6分别独立地是氢或可选取代的（C1-C6）烷基；环A是可选取代的单环或双环碳环或杂环，或具有多达12个环原子的环系；T是公式R-L1-Y1—的基团，其中R是α-氨基酸或α-氨基酸酯基序列，通过定义中的连接基R-L1-Y1—与环A相连。
• ENZYME AND RECEPTOR MODULATION
  申请人：Chroma Therapeutics Ltd

  公开号：US20150126534A1

  公开（公告）日：2015-05-07

  Covalent conjugation of an alpha amino acid ester to a modulator of the activity of a target intracellular enzyme or receptor, wherein the ester group of the conjugate is hydrolysable by one or more intracellular carboxylesterase enzymes to the corresponding acid, leads to accumulation of the carboxylic acid hydrolysis product in the cell and enables improved or more prolonged enzyme or receptor modulation relative to the unconjugated modulator.

  将α-氨基酸酯共价连接到靶向细胞内酶或受体活性调节剂上，其中共轭物的酯基可被一个或多个细胞内羧酸酯酶水解为相应的酸，导致羧酸水解产物在细胞内积累，并相对于未共轭的调节剂实现改善或更长时间的酶或受体调节。
• Quinoline and quinoxaline derivatives as inhibitors of kinase enzymatic activity
  申请人：Davidson Alan Hornsby

  公开号：US20090131461A1

  公开（公告）日：2009-05-21

  Compounds of formula (IA) or (IB), are inhibitors of aurora kinase activity: Formula (IA), (IB) wherein -L1Y1-[CH2]z- is a linker radical wherein Y 1 , L 1 and z are as defined in the claims; R 6 is C 1 -C 4 alkoxy, hydrogen or halo; W represents a bond, —CH 2 —, —O—, —S—, —S(═O) 2 —, or NR 5 — where R 5 is hydrogen or C 1 -C 4 alkyl; Q is ═N—, ═CH— or ═C(X 1 )— wherein X is cyano, cyclopropyl or halo; linker radicals L are as defined in the claims; R is a radical of formula (X) or (Y): wherein R 1 is a carboxylic acid group (—COOH), or an ester group which is hydrolysable by one or more intracellular carboxylesterase enzymes to a carboxylic acid group; R 4 is hydrogen; or optionally substituted C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, aryl, aryl(C 1 -C 6 alkyl)-, heteroaryl, heteroaryl(C 1 -C 6 alkyl)-, —(C═O)R 3 , —(C═O)OR 3 , or —(C═O)NR 3 wherein R 3 is hydrogen or optionally substituted (C 1 -C 6 )alkyl, C 3 -C 7 cycloalkyl, aryl, aryl(C 1 -C 6 alkyl)-, heteroaryl, or heteroaryl(C 1 -C 6 alkyl)-; R 4 1 is hydrogen or optionally substituted C 1 -C 6 alkyl; and D is a mono-cyclic heterocyclic ring of 5 or 6 ring atoms.

  公式（IA）或（IB）的化合物是aurora激酶活性的抑制剂：公式（IA），（IB）其中-L1Y1-[CH2]z-是一个连接基团，其中Y1，L1和z如权利要求中所定义；R6是C1-C4烷氧基，氢或卤素；W代表键，—CH2—，—O—，—S—，—S（═O）2—或NR5—，其中R5是氢或C1-C4烷基；Q是═N—，═CH—或═C（X1）—，其中X是氰基，环丙基或卤素；连接基团L如权利要求中所定义；R是公式（X）或（Y）的基团：其中R1是羧酸基（—COOH），或可由一个或多个细胞内羧酸酯酶水解为羧酸基的酯基团；R4是氢；或者是可选的取代C1-C6烷基，C3-C7环烷基，芳基，芳基（C1-C6烷基）-，杂环芳基，杂环芳基（C1-C6烷基）-，—（C═O）R3，—（C═O）OR3或—（C═O）NR3，其中R3是氢或可选的取代（C1-C6）烷基，C3-C7环烷基，芳基，芳基（C1-C6烷基）-，杂环芳基或杂环芳基（C1-C6烷基）-；R41是氢或可选的取代C1-C6烷基；D是一个由5或6个环原子组成的单环杂环。
• Enzyme and Receptor Modulation
  申请人：Davidson Alan Hornsby

  公开号：US20090215800A1

  公开（公告）日：2009-08-27

  Covalent conjugation of an alpha amino acid ester to a modulator of the activity of a target intracellular enzyme or receptor, wherein the ester group of the conjugate is hydrolysable by one or more intracellular carboxylesterase enzymes to the corresponding acid, leads to accumulation of the carboxylic acid hydrolysis product in the cell and enables improved or more prolonged enzyme or receptor modulation relative to the unconjugated modulator.

  将α-氨基酸酯与靶向细胞内酶或受体活性的调节剂共价结合，其中共轭物的酯基可被一个或多个细胞内羧酸酯酶水解为相应的酸，导致羧酸水解产物在细胞内积累，并使相对于未共轭的调节剂，酶或受体的调节改善或更长久。
• Alpha aminoacid ester-drug conjugates hydrolysable by carboxylesterase
  申请人：Chroma Therapeutics Limited

  公开号：EP1964577A2

  公开（公告）日：2008-09-03

  Covalent conjugation of an alpha amino acid ester to a modulator of the activity of a target intracellular enzyme or receptor, wherein the ester group of the conjugate is hydrolysable by one or more intracellular carboxylesterase enzymes to the corresponding acid, leads to accumulation of the carboxylic acid hydrolysis product in the cell and enables improved or more prolonged enzyme or receptor modulation relative to the unconjugated modulator.

  将α-氨基酸酯与细胞内目标酶或受体的活性调节剂共价共轭，其中共轭物的酯基可被一种或多种细胞内羧基酯酶水解为相应的酸，从而导致羧酸水解产物在细胞内积累，与未共轭的调节剂相比，可改善或延长酶或受体的调节作用。