N-[(9H-芴-9-基甲氧基)羰基]-D-天冬氨酸烯丙基酯 | 204246-17-3

• 物质功能分类: 生物 - 细胞培养 - 添加剂
• 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: N-[(9H-芴-9-基甲氧基)羰基]-D-天冬氨酸烯丙基酯
• 中文别名: 芴甲氧羰基-D-天冬氨酸-烯丙酯
• 英文名称: N-alpha-(9-fluorenylmethyloxycarbonyl)-D-aspartic acid alpha-allyl ester
• 英文别名: D-Fmoc-Asp-OAll；Fmoc-D-Asp-OAll；(3R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxo-4-prop-2-enoxybutanoic acid
• CAS: 204246-17-3
• 化学式: C₂₂H₂₁NO₆
• 分子量: 395.412
• InChiKey: ZJMVIWUCCRKNHY-LJQANCHMSA-N

物化性质

• 沸点：
  634.8±55.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  N-[(9H-芴-9-基甲氧基)羰基]-D-天冬氨酸烯丙基酯 在 四(三苯基膦)钯 、 苯硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 2-(4-Hydroxyphenyl)quinoline-4-carbonyl chloride
  参考文献：
  名称：

  Synthesis of enantiomerically pure perhydro-1,4-diazepine-2,5-dione and 1,4-piperazine-2,5-dione derivatives exhibiting potent activity as apoptosis inhibitors

  摘要：

  Apoptosis is the process of programmed cell death and plays a fundamental role in several human diseases. We have previously reported the synthesis of the perhydro-1,4-diazepine-2,5-dione and 1,4-piperazine-2,5-dione derivatives as racemic mixtures. Compounds 1 and 2 showed a potent in vitro and in cellular extracts antiapoptotic activity. In view that the chiral discrimination has been an issue in the development and use of pharmaceutical drugs, the present contribution reports the synthesis of enantiopure peptidomimetics 1 and 2. The biological evaluation of these enantiomers as apoptosis inhibitors is also reported. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.078
• 作为产物：
  描述：

  N-(2-amino-2-oxoethyl)-N-[2-(2,4-dichlorophenyl)ethyl]-2-[(2R)-4-[2-(2,4-dichlorophenyl)ethyl]-1-(2,2-diphenylethyl)-3,6-dioxopiperazin-2-yl]acetamide 在 哌啶 、 N,N'-二异丙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.03h， 生成 N-[(9H-芴-9-基甲氧基)羰基]-D-天冬氨酸烯丙基酯
  参考文献：
  名称：

  Synthesis of enantiomerically pure perhydro-1,4-diazepine-2,5-dione and 1,4-piperazine-2,5-dione derivatives exhibiting potent activity as apoptosis inhibitors

  摘要：

  Apoptosis is the process of programmed cell death and plays a fundamental role in several human diseases. We have previously reported the synthesis of the perhydro-1,4-diazepine-2,5-dione and 1,4-piperazine-2,5-dione derivatives as racemic mixtures. Compounds 1 and 2 showed a potent in vitro and in cellular extracts antiapoptotic activity. In view that the chiral discrimination has been an issue in the development and use of pharmaceutical drugs, the present contribution reports the synthesis of enantiopure peptidomimetics 1 and 2. The biological evaluation of these enantiomers as apoptosis inhibitors is also reported. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.078

文献信息

• Selection of DNA‐Encoded Dynamic Chemical Libraries for Direct Inhibitor Discovery
  作者：Yuqing Deng、Jianzhao Peng、Feng Xiong、Yinan Song、Yu Zhou、Jianfu Zhang、Fong Sang Lam、Chao Xie、Wenyin Shen、Yiran Huang、Ling Meng、Xiaoyu Li

  DOI：10.1002/anie.202005070

  日期：2020.8.24

  that can identify full ligand structures from large‐scale DEDLs. This method is also able to convert unbiased libraries into focused ones targeting specific protein classes. We demonstrated this method by selecting DEDLs against five proteins, and novel inhibitors were identified for all targets. Notably, several selective BD1/BD2 inhibitors were identified from the selections against bromodomain 4 (BRD4)

  动态组合库（DCL）是生物医学研究中配体发现的强大工具。但是，DCL的低多样性阻碍了它们的应用。最近，DCL中已经采用了DNA编码的概念来创建DNA编码的动态库（DEDL）。但是，当前所有的DEDL都仅限于片段识别，并且在选择后需要一个具有挑战性的片段链接过程。我们报告了一种锚定的DEDL方法，该方法可以从大规模DEDL中识别出完整的配体结构。这种方法还能够将无偏文库转换为针对特定蛋白质类别的集中文库。我们通过选择针对五种蛋白质的DEDLs证明了这种方法，并为所有靶标确定了新型抑制剂。值得注意的是 从针对重要的抗癌药物靶标bromodomain 4（BRD4）的选择中鉴定出了几种选择性的BD1 / BD2抑制剂。这项工作可以为抑制剂发现提供广泛适用的方法。
• [EN] ANTIBIOTIC NATURAL PRODUCT ANALOGUES<br/>[FR] ANALOGUES DE PRODUITS NATURELS ANTIBIOTIQUES
  申请人：UNIV BELFAST

  公开号：WO2022162332A1

  公开（公告）日：2022-08-04

  A compound of formula (I) or formula (II) including tautomeric or stereochemically isomeric forms thereof, wherein: R1represents C1-20 alkyl, C2-20 alkenyl, C6-20 aryl, or C4-20 heterocyclyl, each optionally substituted with one or more Y groups, R2ato R21each independently represents H, C1-10 alkyl, C2-10 alkenyl, C6-12 aryl, or C4-12 heterocyclyl, each optionally substituted with one or more Y groups, R3represents H, C1-10 alkyl, C2-10 alkenyl, C6-12 aryl, or C4-12 heterocyclyl, each optionally substituted with one or more Y groups, X represents NH, S or O, each Y independently represents cyano, halogen, N3, -C(O)RZ, -C(0)0Rz, -0C(0)Rz, -C(0)NHRZ, -NHC(O) Rz, -NHC(0)NHRZ, - NHC(NH)NHRZ, -NHC(0)0Rz, -0C(0)NHRz, -0S(0)2RZ, -S(0)2NHRZ, -NHS(0)2RZ, -SRZ, -NRZZ or -ORz, and each Rzindependently represents H, C1-10 alkyl, C2-10 alkenyl, C6-10 aryl, or C4-10 heterocyclyl; or an N-oxide thereof or a pharmaceutically acceptable salt thereof or a pharmaceutically acceptable solvate thereof; and wherein formula (I) excludes laterocidine, wherein formula (I) excludes relacidine A, and wherein formula (I) excludes relacidine B. A pharmaceutical composition comprising the compound. The compounds and pharmaceutical compositions are useful as antibiotics.

  化合物的化学式为(I)或(II)，包括其互变异构体或立体化学异构体，其中：R1代表C1-20烷基，C2-20烯基，C6-20芳基或C4-20杂环基，每个都可以选择地用一个或多个Y基取代，R2至R21各自独立地代表H，C1-10烷基，C2-10烯基，C6-12芳基或C4-12杂环基，每个都可以选择地用一个或多个Y基取代，R3代表H，C1-10烷基，C2-10烯基，C6-12芳基或C4-12杂环基，每个都可以选择地用一个或多个Y基取代，X代表NH，S或O，每个Y独立地代表氰基，卤素，N3，-C（O）RZ，-C（0）0Rz，-0C（0）Rz，-C（0）NHRZ，-NHC（O）Rz，-NHC（0）NHRZ，-NHC（NH）NHRZ，-NHC（0）0Rz，-0C（0）NHRz，-0S（0）2RZ，-S（0）2NHRZ，-NHS（0）2RZ，-SRZ，-NRZZ或-ORz，每个Rz独立地代表H，C1-10烷基，C2-10烯基，C6-10芳基或C4-10杂环基；或其N-氧化物或药学上可接受的盐或药学上可接受的溶剂；其中化学式(I)不包括laterocidine，化学式(I)不包括relacidine A，化学式(I)不包括relacidine B。包括该化合物的制药组合物。该化合物和制药组合物可用作抗生素。
• [EN] SYNTHETIC PROCESS FOR THE MANUFACTURE OF PIPECOLIDEPSIN COMPOUNDS<br/>[FR] PROCÉDÉ DE SYNTHÈSE POUR LA FABRICATION DE COMPOSÉS DE PIPÉCOLIDEPSINE
  申请人：PHARMA MAR SA

  公开号：WO2014108526A1

  公开（公告）日：2014-07-17

  (I) wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, n and Y are as described. The invention provides a process for the synthesis of complex pipecolidepsin and related compounds of formula (I), opening a new field of compounds with useful biological properties. The invention also provides intermediates, useful in the synthesis of compounds of formula (I).
• Synthesis of enantiomerically pure perhydro-1,4-diazepine-2,5-dione and 1,4-piperazine-2,5-dione derivatives exhibiting potent activity as apoptosis inhibitors
  作者：Alejandra Moure、Mar Orzáez、Mónica Sancho、Angel Messeguer

  DOI：10.1016/j.bmcl.2012.09.078

  日期：2012.12

  Apoptosis is the process of programmed cell death and plays a fundamental role in several human diseases. We have previously reported the synthesis of the perhydro-1,4-diazepine-2,5-dione and 1,4-piperazine-2,5-dione derivatives as racemic mixtures. Compounds 1 and 2 showed a potent in vitro and in cellular extracts antiapoptotic activity. In view that the chiral discrimination has been an issue in the development and use of pharmaceutical drugs, the present contribution reports the synthesis of enantiopure peptidomimetics 1 and 2. The biological evaluation of these enantiomers as apoptosis inhibitors is also reported. (C) 2012 Elsevier Ltd. All rights reserved.