4-benzyloxy-N-methanesulfonyl-phenylalanine-methylester | 174701-15-6

• 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: 4-benzyloxy-N-methanesulfonyl-phenylalanine-methylester
• 英文别名: methyl (2S)-2-(methanesulfonamido)-3-(4-phenylmethoxyphenyl)propanoate
• CAS: 174701-15-6
• 化学式: C₁₈H₂₁NO₅S
• 分子量: 363.434
• InChiKey: PEWMYOGUIVOHOE-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-benzyloxy-N-methanesulfonyl-phenylalanine-methylester 在 羟胺钾盐 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 28.0h， 生成 (2S)-N-hydroxy-2-(methanesulfonamido)-3-(4-phenylmethoxyphenyl)propanamide
  参考文献：
  名称：

  Design, synthesis and evaluation of novel metalloproteinase inhibitors based on l-tyrosine scaffold

  摘要：

  A series of novel L-tyrosine derivatives were designed, synthesized and assayed for their inhibitory activities on matrix metalloproteinase 2 (MMP-2) and histone deacetylase 8 (HDAC-8). The results showed that these L-tyrosine derivatives exhibited inhibitory profiles against MMP-2 and HDAC-8. The compounds 6h (IC50 = 0.013 +/- 0.001 mu M) and 6j (IC50 = 0.017 +/- 0.001 mu M) were equal potent MMP-2 inhibitors to the positive control NNGH (IC50 = 0.014 +/- 0.001 mu M). As for HDAC-8 inhibition, some of the hydroxamate compounds, such as 6d (IC50 = 3.6 +/- 0.2 mu M) and 6c (IC50 = 5.8 +/- 0.5 mu M), were equal potent to the positive control SAHA (IC50 = 1.6 +/- 0.1 mu M). Structure-activity relationships were also briefly discussed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.014
• 作为产物：
  描述：

  Boc-L-酪氨酸甲酯 在 sodium carbonate 、 potassium carbonate 、 三氟乙酸 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 15.0h， 生成 4-benzyloxy-N-methanesulfonyl-phenylalanine-methylester
  参考文献：
  名称：

  Design, synthesis and evaluation of novel metalloproteinase inhibitors based on l-tyrosine scaffold

  摘要：

  A series of novel L-tyrosine derivatives were designed, synthesized and assayed for their inhibitory activities on matrix metalloproteinase 2 (MMP-2) and histone deacetylase 8 (HDAC-8). The results showed that these L-tyrosine derivatives exhibited inhibitory profiles against MMP-2 and HDAC-8. The compounds 6h (IC50 = 0.013 +/- 0.001 mu M) and 6j (IC50 = 0.017 +/- 0.001 mu M) were equal potent MMP-2 inhibitors to the positive control NNGH (IC50 = 0.014 +/- 0.001 mu M). As for HDAC-8 inhibition, some of the hydroxamate compounds, such as 6d (IC50 = 3.6 +/- 0.2 mu M) and 6c (IC50 = 5.8 +/- 0.5 mu M), were equal potent to the positive control SAHA (IC50 = 1.6 +/- 0.1 mu M). Structure-activity relationships were also briefly discussed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.014

文献信息

• CONJUGATES MADE OF METAL COMPLEXES AND OLIGONUCLEOTIDES, AGENTS CONTAINING THE CONJUGATES, THEIR USE IN RADIODIAGNOSIS AS WELL AS PROCESS FOR THEIR PRODUCTION
  申请人：——

  公开号：US20020077306A1

  公开（公告）日：2002-06-20

  This invention relates to chemically modified oligo-nucleotide conjugates that contain a complexing agent or complex that is bound by a connecting component to the oligonucleotides. In this case, the oligonucleotides are modified in a way that prevents or at least significantly inhibits the degradation by naturally occurring nucleases. The oligonucleotide radical can bond specifically and with high bonding affinity to target structures and can thus produce a specific therapeutic or diagnostic effect by the bound complexing agent or complex.

  这项发明涉及化学修饰的寡核苷酸共轭物，其中包含一个由连接组分与寡核苷酸结合的络合剂或络合物。在这种情况下，寡核苷酸以一种方式进行了修饰，以防止或至少显著抑制天然核酸酶的降解。寡核苷酸基团可以与靶结构特异性地结合，并且可以通过结合的络合剂或络合物产生特异的治疗或诊断效果。
• CONJUGATES MADE OF METAL COMPLEXES AND OLIGONUCLEOTIDES
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0777498A1

  公开（公告）日：1997-06-11
• [EN] CONJUGATES MADE OF METAL COMPLEXES AND OLIGONUCLEOTIDES<br/>[FR] CONJUGUES CONSTITUES DE COMPLEXES METALLIQUES ET D'OLIGONUCLEOTIDES
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：WO1996002274A1

  公开（公告）日：1996-02-01

  (EN) This invention relates to chemically modified oligonucleotide conjugates that contain a complexing agent or complex that is bound by a connecting component to the oligonucleotides. In this case, the oligonucleotides are modified in a way that prevents or at least significantly inhibits the degradation by naturally occurring nucleases. The oligonucleotide radical can bond specifically and with high bonding affinity to target structures and can thus produce a specific therapeutic or diagnostic effect by the bound complexing agent or complex.(FR) L'invention concerne des conjugués d'oligonucléotides modifés chimiquement contenant un agent de formation de complexes ou un complexe lié par un consituant de liaison aux oligonucléotides. Dans ce cas, les oligonucléotides sont modifiés d'une manière empêchant ou au moins inhibant sensiblement la dégradation par des nucléases naturelles. Le radical oligonucléotidique peut se lier spécifiquement, avec une haute affinité de liaison, à des structures cibles, il peut par conséquent produire un effet thérapeutique ou diagnostique spécifique par l'agent de formation de complexes ou le complexe lié.
• Design, synthesis and evaluation of novel metalloproteinase inhibitors based on l-tyrosine scaffold
  作者：Xian-Chao Cheng、Run-Ling Wang、Zhen-Ke Dong、Jing Li、Yao-Yuan Li、Rong-Rong Li

  DOI：10.1016/j.bmc.2012.08.014

  日期：2012.10

  A series of novel L-tyrosine derivatives were designed, synthesized and assayed for their inhibitory activities on matrix metalloproteinase 2 (MMP-2) and histone deacetylase 8 (HDAC-8). The results showed that these L-tyrosine derivatives exhibited inhibitory profiles against MMP-2 and HDAC-8. The compounds 6h (IC50 = 0.013 +/- 0.001 mu M) and 6j (IC50 = 0.017 +/- 0.001 mu M) were equal potent MMP-2 inhibitors to the positive control NNGH (IC50 = 0.014 +/- 0.001 mu M). As for HDAC-8 inhibition, some of the hydroxamate compounds, such as 6d (IC50 = 3.6 +/- 0.2 mu M) and 6c (IC50 = 5.8 +/- 0.5 mu M), were equal potent to the positive control SAHA (IC50 = 1.6 +/- 0.1 mu M). Structure-activity relationships were also briefly discussed. (C) 2012 Elsevier Ltd. All rights reserved.