methyl N-((benzyloxy)carbonyl)-O-(2-ethoxy-2-oxoethyl)-L-serinate | 1042070-13-2

• 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: methyl N-((benzyloxy)carbonyl)-O-(2-ethoxy-2-oxoethyl)-L-serinate
• CAS: 1042070-13-2
• 化学式: C₁₆H₂₁NO₇
• 分子量: 339.345
• InChiKey: IGCHGIUICJXURG-ZDUSSCGKSA-N

物化性质

• 沸点：
  479.1±45.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  methyl N-((benzyloxy)carbonyl)-O-(2-ethoxy-2-oxoethyl)-L-serinate 在 氨 作用下， 以 甲醇 为溶剂， 以100%的产率得到
  参考文献：
  名称：

  Design and synthesis of 6-amino-1,4-oxazepane-3,5-dione derivatives as novel broad spectrum anticonvulsants

  摘要：

  Based on the structural estimations of the typical anticonvulsant drugs, a series of 6-amino-1,4-oxazepane-3,5-dione derivatives, novel structures of 7-membered heterocyclic imides, which were hybridized with pharmacophores such as cyclic imide and N-CO-C-N group in their molecule were designed and synthesized. Their anticonvulsant activities were evaluated by the maximal electroshock induced seizure (MES) and subcutaneous pentylenetetrazole (PTZ) tests. Almost all the designed compounds except 1c and 1f showed comparable anticonvulsant activities in at least one of the anticonvulsant tests. Moreover, some of the tested compounds exhibited moderate anticonvulsant activities in both MES and PTZ tests. From these results, 6-amino-1,4-oxazepane3,5-dione derivatives could be recommended as novel structures of broad spectrum anticonvulsants. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.067
• 作为产物：
  描述：

  N-苄氧羰酰基-L-丝氨酸甲酯 、 溴乙酸乙酯 在 sodium hydride 作用下， 以 乙腈 为溶剂， 以70%的产率得到methyl N-((benzyloxy)carbonyl)-O-(2-ethoxy-2-oxoethyl)-L-serinate
  参考文献：
  名称：

  Design and synthesis of 6-amino-1,4-oxazepane-3,5-dione derivatives as novel broad spectrum anticonvulsants

  摘要：

  Based on the structural estimations of the typical anticonvulsant drugs, a series of 6-amino-1,4-oxazepane-3,5-dione derivatives, novel structures of 7-membered heterocyclic imides, which were hybridized with pharmacophores such as cyclic imide and N-CO-C-N group in their molecule were designed and synthesized. Their anticonvulsant activities were evaluated by the maximal electroshock induced seizure (MES) and subcutaneous pentylenetetrazole (PTZ) tests. Almost all the designed compounds except 1c and 1f showed comparable anticonvulsant activities in at least one of the anticonvulsant tests. Moreover, some of the tested compounds exhibited moderate anticonvulsant activities in both MES and PTZ tests. From these results, 6-amino-1,4-oxazepane3,5-dione derivatives could be recommended as novel structures of broad spectrum anticonvulsants. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.067

文献信息

• Elucidating the Structural Requirement of Uridylpeptide Antibiotics for Antibacterial Activity
  作者：Yuma Terasawa、Chisato Sataka、Toyotaka Sato、Kazuki Yamamoto、Yukari Fukushima、Chie Nakajima、Yasuhiko Suzuki、Akira Katsuyama、Takanori Matsumaru、Fumika Yakushiji、Shin-ichi Yokota、Satoshi Ichikawa

  DOI：10.1021/acs.jmedchem.0c00973

  日期：2020.9.10

  The synthesis and biological evaluation of analogues of uridylpeptide antibiotics were described, and the molecular interaction between the 3′-hydroxy analogue of mureidomycin A (3′-hydroxymureidomycin A) and its target enzyme, phospho-MurNAc-pentapeptide transferase (MraY), was analyzed in detail. The structure–activity relationship (SAR) involving MraY inhibition suggests that the side chain at the

  描述了尿苷肽抗生素类似物的合成和生物学评估，并证明了莫来霉素A（3'-羟基尿素霉素A）的3'-羟基类似物与其靶酶磷酸-MurNAc-五肽转移酶（MraY）之间的分子相互作用。详细分析。涉及MraY抑制的结构活性关系（SAR）表明，尿素-二肽部分的侧链不影响MraY抑制。但是，抗铜绿假单胞菌活性形成了鲜明的对比，而尿素-二肽基序是关键的贡献者。还建议核苷肽渗透酶NppA1A2BCD负责3'-羟基mureidomycin A进入细胞质的转运。进一步进行了3'-羟基mureidomycin A尿素-二肽部分的系统SAR分析，并确定了抗菌活性。该研究为基于尿苷肽抗生素的类似物的合理设计提供了指导。
• Expanding the scope of N → S acyl transfer in native peptide sequences
  作者：Ben Cowper、Leila Shariff、Wenjie Chen、Samantha M. Gibson、Wei-Li Di、Derek Macmillan

  DOI：10.1039/c5ob01029b

  日期：——

  influence N → S acyl transfer in native peptide sequences, and discovery of new reagents that facilitate it, will be key to expanding its scope and applicability. Here, through a study of short model peptides in thioester formation and cyclisation reactions, we demonstrate that a wider variety of Xaa-Cys motifs than originally envisaged are capable of undergoing efficient N → S acyl transfer. We present

  了解影响天然肽序列中N→S酰基转移的因素，并发现促进其转移的新试剂，将是扩大其范围和适用性的关键。在这里，通过对硫酯形成和环化反应中的短模型肽的研究，我们证明了比最初设想的更广泛的Xaa-Cys基序能够进行有效的N→S酰基转移。我们提供了一组代表性氨基酸的硫酯形成和环化的相对速率的数据，并显示了这种扩大的范围如何可以应用于天然蛋白酶抑制剂向日葵胰蛋白酶抑制剂1（SFTI-1）的生产。
• A Small-Molecule Drug Conjugate for the Treatment of Carbonic Anhydrase IX Expressing Tumors
  作者：Nikolaus Krall、Francesca Pretto、Willy Decurtins、Gonçalo J. L. Bernardes、Claudiu T. Supuran、Dario Neri

  DOI：10.1002/anie.201310709

  日期：2014.4.14

  Antibody–drug conjugates are a very promising class of new anticancer agents, but the use of small‐molecule ligands for the targeted delivery of cytotoxic drugs into solid tumors is less well established. Here, we describe the first small‐molecule drug conjugates for the treatment of carbonic anhydrase IX expressing solid tumors. Using ligand–dye conjugates we demonstrate that such molecules can preferentially

  抗体-药物结合物是一类非常有前途的新型抗癌药，但将小分子配体用于将细胞毒性药物靶向递送至实体瘤的用途尚不十分清楚。在这里，我们描述了第一种用于治疗表达碳酸酐酶IX的实体瘤的小分子药物偶联物。使用配体-染料偶联物，我们证明了此类分子可以优先在抗原阳性病变内积聚，具有快速的靶向动力学和良好的肿瘤穿透特性，并且易于通过全合成获得。二硫键连接的药物偶联物，以美登木素生物碱DM1为细胞毒性有效载荷，以乙酰唑胺衍生物为靶向配体，在体内SKRC52肾细胞癌中表现出有效的抗肿瘤作用。此外，它优于舒尼替尼和索拉非尼，
• [EN] SMALL MOLECULE DRUG CONJUGATES<br/>[FR] CONJUGUÉS DE MÉDICAMENTS À PETITES MOLÉCULES
  申请人：EIDGENOESS TECH HOCHSCHULE

  公开号：WO2015114171A1

  公开（公告）日：2015-08-06

  A targeted therapeutic agent comprising a compound of formula (I): B–L–D, wherein: B is a low molecular weight binding moiety for Carbonic Anhydrase IX (CAIX); D is a drug moiety; and L is a linker group that undergoes cleavage in vivo for releasing said drug moiety in an active form. The drug moiety is suitably a cytotoxic agent for targeted delivery to cancer cells expressing CAIX. The binding moiety B suitably comprises a sulfonamidothiadiazole moiety. The binding moiety B may comprise one, two or more groups capable of binding to CAIX. The linker group suitably comprises a disulfide bond and/or a triazole group and/or a cleavable peptide group.

  一种靶向治疗剂，包括化合物的结构式(I)：B–L–D，其中：B是一种低分子量结合基团，用于碳酸酐酶IX（CAIX）；D是一种药物基团；L是一个在体内发生裂解以释放所述药物基团的连接基团。药物基团适宜是一种针对表达CAIX的癌细胞的细胞毒性药剂。结合基团B适宜包括磺胺基噻二唑基团。结合基团B可以包括一个、两个或更多能够结合CAIX的基团。连接基团适宜包括二硫键和/或三唑基团和/或可裂解的肽基团。
• The stereodynamics of macrocyclic succinimide-thioethers
  作者：Stefan Lenz、Philip Horx、Armin Geyer

  DOI：10.1002/psc.3075

  日期：2018.4

  macrocyclisation of 5 designed pentapeptides with the ringsize of hexapeptides because they incorporate the succinimide thioether (4‐8). Both succinimide diastereomers are observed in the constrained macrocyclic rings in each case. In spite of the low diastereoselectivity of the macrocyclisation reaction, there is a significant influence of the amino acid environment on the epimerization rate of the succinimide

  马来酰亚胺-硫醇偶联是一种流行的生物缀合策略，但是对于在生物聚合物环境中形成的琥珀酰亚胺硫醚的立体选择性和立体动力学知之甚少。我们使用的硫醇1,4-加成5个设计的五肽与六肽的ringsize的大环，因为它们包含的琥珀酰亚胺硫醚（4 - 8）。两种琥珀酰亚胺非对映异构体均在受限的大环中被观察到。尽管大环化反应的非对映选择性低，但是氨基酸环境对琥珀酰亚胺的差向异构化速率有显着影响。当Gly为琥珀酰亚胺（第8号肽）的氨基酸时，其在室温下的半衰期可短至几个小时）。相反，对于肽4中琥珀酰亚胺的d -Phe C-末端，即使经过数周也未检测到差向异构。少量的实例已经显示出差向异构率的差异可能有多大，并且本地环境具有重大影响。连接位点附近氨基酸的变化为合成以稳定和可分离的非对映异构体形式存在的生物缀合物指明了道路。