N-Boc-N-methyl-L-leucyl-D-lactic acid | 157567-62-9

• 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-Boc-N-methyl-L-leucyl-D-lactic acid
• 英文别名: (R)-2-((S)-2-(tert-butoxycarbonyl(methyl)amino)-4-methylpentanoyloxy)propanoic acid；Boc-L-MeLeu-D-Lac-OH；(2R)-2-[(2S)-4-methyl-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pentanoyl]oxypropanoic acid
• CAS: 157567-62-9
• 化学式: C₁₅H₂₇NO₆
• 分子量: 317.382
• InChiKey: HHYZGBLKORQQOK-MNOVXSKESA-N

物化性质

• 沸点：
  423.5±38.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-Boc-N-methyl-L-leucyl-D-lactic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 1-(tert-butyl) 2-((4R,7S,10R,13S,16R,19S,22R)-4,16-dibenzyl-7,13,19-triisobutyl-8,10,14,20-tetramethyl-3,6,9,12,15,18,21-heptaoxo-1-phenyl-2,5,11,17-tetraoxa-8,14,20-triazatricosan-22-yl) (S)-pyrrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  Restricted Conformation Analogues of an Anthelmintic Cyclodepsipeptide

  摘要：

  Six analogues of the anthelmintic cyclodepsipeptide PF1022A were prepared, each containing a small ring fused to the macrocycle to restrict the number of conformations the larger ring can adopt. It was anticipated that such conformational changes could lead to enhanced biological activity and selectivity. The analogues form two series of three members each. In one series, a carbon-based molecular bridge joins the methyl of a leucine residue with the methyl of its closest lactic acid residue to form five-, six-, and seven-membered lactam rings. In the second series, a leucine residue is replaced with five-, six-, and seven-membered nitrogen heterocycles. Decreasing the size of the small ring in the lactam. series increasingly distorts the macrocycle and consistently decreases activity relative to PF1022A. In the leucine series, a similar trend is observed. Molecular modeling of PF1022A along with the analogues described herein suggests that the ability to exist in a highly symmetrical conformational state is a necessary condition for biological activity.

  DOI：

  10.1021/jm020482k
• 作为产物：
  描述：

  N-t-butoxycarbonyl-N-methyl-L-leucine 在 palladium 10% on activated carbon 、 氢气 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 3.0h， 生成 N-Boc-N-methyl-L-leucyl-D-lactic acid
  参考文献：
  名称：

  驱虫环十八肽PF1022A和艾莫德苷的片段固相全合成

  摘要：

  环缩肽、PF1022 和 verticilide 家族代表了多种多样的非常有趣的天然产物，因为它们具有多种生物活性。然而，到目前为止，还没有完成这些化合物的切实可行的固相合成，这可能是由于 N-甲基氨基酸和羟基羧酸的组合存在问题。我们在此报告了一种在 Kaiser 和 Wang 树脂上有效合成驱虫剂 PF1022A 及其商业模拟物艾莫德苷的方法。我们的协议为环缩肽库的固相合成提供了基础，具有很高的驱虫、抗菌或杀虫活性。

  DOI：

  10.1002/ejoc.201101421

文献信息

• [EN] ANTHELMINTIC DEPSIPEPTIDE COMPOUNDS<br/>[FR] COMPOSÉS DEPSIPEPTIDIQUES ANTHELMINTHIQUES
  申请人：MERIAL INC

  公开号：WO2018093920A1

  公开（公告）日：2018-05-24

  The present invention provides cyclic depsipeptide compounds of formula (I) wherein the stereochemical configuration of at least one carbon atom bearing the groups Cy1, Cy2, R1, R2, R3, R4, Ra and Rb is inverted compared with the naturally occurring cyclic depsipeptide PF1022A. The invention also provides compositions comprising the compounds that are effective against parasites that harm animals. The compounds and compositions may be used for combating parasites in or on mammals and birds. The invention also provides for an improved method for eradicating, controlling and preventing parasite infestation in birds and mammals.

  本发明提供了公式（I）的环状脱氨肽化合物，其中至少一个碳原子的立体化学构型与自然存在的环状脱氨肽PF1022A的基团Cy1、Cy2、R1、R2、R3、R4、Ra和Rb相比发生了倒置。该发明还提供了包含这些化合物的组合物，对危害动物的寄生虫具有有效性。这些化合物和组合物可用于对抗哺乳动物和鸟类体内或体表的寄生虫。该发明还提供了一种改进的方法，用于根除、控制和预防鸟类和哺乳动物的寄生虫感染。
• Solid-phase synthesis of cyclooctadepsipeptide PF1022A analogs using a cyclization-cleavage method with oxime resin
  作者：Byung H. Lee

  DOI：10.1016/s0040-4039(96)02454-9

  日期：1997.2

  N-Methyloctadepsipeptides attached to an oxime resin were cyclized by heating them in refluxing ethyl acetate for 2 days to give cyclooctadepsipeptide PF1022A analogs.

  通过在回流的乙酸乙酯中加热它们使与肟树脂连接的N-甲基八肽肽环化2天，从而得到环八肽肽PF1022A类似物。
• Anthelmintic depsipeptide compounds
  申请人：BOEHRINGER INGELHEIM ANIMAL HEALTH USA INC.

  公开号：US10344056B2

  公开（公告）日：2019-07-09

  The present invention provides cyclic depsipeptide compounds of formula (I) and compositions comprising the compounds that are effective against parasites that harm animals, including humans. The compounds and compositions may be used for combating parasites in or on animals including mammals and birds. The invention also provides for an improved method for eradicating, controlling and preventing parasite infestation in animals, including birds and mammals.

  本发明提供了式(I)的环状去肽化合物和含有该化合物的组合物，它们能有效地防治危害动物（包括人类）的寄生虫。这些化合物和组合物可用于防治包括哺乳动物和鸟类在内的动物体内或身上的寄生虫。本发明还提供了一种根除、控制和预防动物（包括鸟类和哺乳动物）体内寄生虫侵扰的改进方法。
• Generation of a small library of cyclodepsipeptide PF1022A analogues using a cyclization-Cleavage method with oxime resin
  作者：B Lee

  DOI：10.1016/s0960-894x(01)00748-x

  日期：2002.2.11

  N-Methyloctadepsipeptides attached to an oxime resin were cyclized by heating them in refluxing ethyl acetate for 2 days to give cyclodepsipeptide PF1022A analogues. By using this method, we generated a small library of PF 1022A analogues (2), several of which possessed anthelmintic activity, based on an in vitro assay. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Ohyama, Makoto; Iinuma, Katsuharu; Isogai, Akira, Bioscience, Biotechnology and Biochemistry, 1994, vol. 58, # 6, p. 1193 - 1194
  作者：Ohyama, Makoto、Iinuma, Katsuharu、Isogai, Akira、Suzuki, Akinori

  DOI：——

  日期：——