N²-(tert-butoxycarbonyl)-N³-(4-methoxyfumaroyl)-L-2,3-diaminopropanoic acid | 104302-84-3

• 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: N²-(tert-butoxycarbonyl)-N³-(4-methoxyfumaroyl)-L-2,3-diaminopropanoic acid
• 英文别名: (2S)-2-(tert-butoxycarbonylamino)-3-[[(E)-4-methoxy-4-oxo-but-2-enoyl]amino]propanoic acid；(2S)-3-[[(E)-4-methoxy-4-oxobut-2-enoyl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 104302-84-3
• 化学式: C₁₃H₂₀N₂O₇
• 分子量: 316.311
• InChiKey: CUDUYMTYEPVOCV-GJIOHYHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N²-(tert-butoxycarbonyl)-N³-(4-methoxyfumaroyl)-L-2,3-diaminopropanoic acid 在 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 N-(N²-(tert-butoxycarbonyl)-N³-(4-methoxyfumaroyl)-L-2,3-diaminopropanoyl)glycine
  参考文献：
  名称：

  新型抗菌剂N3-（4-甲氧基富马酰基）-L-2,3-二氨基丙酸二肽的合成及生物学性质。

  摘要：

  合成了一系列具有N3-（4-甲氧基富马酰基）-L-2,3-二氨基丙酸（FMDP）的二肽，它们是细菌和真菌不可逆的葡萄糖胺-6-磷酸合成酶抑制剂，其抗菌和抗真菌特性体外评估。结果表明，这些肽抑制了许多测试微生物的生长，尤其是致病真菌白色念珠菌。竞争性拮抗作用研究的结果表明，通过作为药物递送系统的肽渗透酶进行的肽的特异性肽运输，并且由于抑制了葡糖胺的产生，提供了对细胞作用的高选择性的证据。

  DOI：

  10.1021/jm00393a005
• 作为产物：
  描述：

  (S)-3-amino-2-tert-butoxycarbonylaminopropionic acid 、 富马酸单甲酯 以76%的产率得到
  参考文献：
  名称：

  ANDRUSZKIEWICZ, RYSZARD;CHMARA, HENRYK;MILEWSKI, SLAWOMIR;BOROWSKI, EDWAR+

  摘要：

  DOI：

文献信息

• Amide and ester derivatives of N3-(4-methoxyfumaroyl)-(S)-2,3-diaminopropanoic acid
  作者：Dorota Zgódka、Robert Jędrzejczak、Sławomir Milewski、Edward Borowski

  DOI：10.1016/s0968-0896(00)00315-1

  日期：2001.4

  ester derivatives of a glutamine analogue, N3-(4-methoxyfumaroyl)-(S)-2,3-diaminopropanoic acid (FMDP) (1-8), were synthesized and evaluated for the inhibitory activity in regard to glucosamine-6-phosphate synthase from Candida albicans. The syntheses were accomplished by the reaction of N2-tert-butoxycarbonyl-N3-(4-methoxyfumaroyl)-(S)-2,3-diaminopropanoic acid (BocFMDP) with the corresponding amines

  合成了谷氨酰胺类似物N3-（4-甲氧基富马酰基）-（S）-2,3-二氨基丙酸（FMDP）（1-8）的几种酰胺和酯衍生物，并评估了其对葡萄糖胺-来自白色念珠菌的6-磷酸合酶。合成是通过N2-叔丁氧基羰基-N3-（4-甲氧基富马酰基）-（S）-2,3-二氨基丙酸（BocFMDP）与相应的胺反应生成FMDP酰胺（1-4）或用卤代烷与相应的FMDP酯（5-8）。在合成的化合物中，FMDP的乙酰氧基甲酯是该酶的最有效抑制剂。与FMDP（4 microM）相比，它的IC50值等于11.5 microM。FMDP的甲基和烯丙基酯和N-己基-N-甲基酰胺表现出中等的酶抑制活性。
• The synthesis and biological activity of lipophilic derivatives of bicine conjugated with<i>N</i>³-(4-methoxyfumaroyl)-<scp>L</scp>-2,3-diaminopropanoic acid (FMDP)—an inhibitor of glucosamine-6-phosphate synthase
  作者：Dominik Koszel、Izabela Łącka、Katarzyna Kozłowska-Tylingo、Ryszard Andruszkiewicz

  DOI：10.3109/14756366.2011.582039

  日期：2012.4.1

  A series of bis-N,N-(2-hydroxyethyl)glycine (bicine) derivatives, conjugated with an inhibitor of glucosamine-6-phosphate synthase, have been synthesized and their lipophilic and antifungal properties have been tested. The obtained compounds demonstrated higher lipophilicity than free inhibitor (FMDP) and, in consequence, an increased potential to cross the cytoplasmic membrane. All the tested compounds show better antifungal activity than parent compound.
• Synthesis and biological evaluation of dipeptidyl and tripeptidyl polyoxin and nikkomycin analogs as anticandidal prodrugs
  作者：Eduardo Krainer、Jeffrey M. Becker、Fred Naider

  DOI：10.1021/jm00105a026

  日期：1991.1

  Nine analogues (1-5, 9-12) of the peptidyl nucleoside antibiotics nikkomycin and polyoxin were synthesized and tested for their biological properties against different strains of the pathogenic yeast Candida albicans. The tripeptidyl series of analogues (1-5) was designed to behave as prodrugs, releasing a toxic moiety upon enzymatic hydrolysis inside the cell. The dipeptidyl series (9-12) was designed as double-targeted drugs, being themselves toxic and releasing a toxic amino acid upon hydrolysis. All the analogues were prepared by coupling suitably protected amino acid p-nitrophenyl esters to 1-(5'-amino-5'-deoxy-alpha-D-allofuranuronosyl)uracil (UPOC) or the corresponding polyoxins and nikkomycins, with subsequent removal of the protecting group. Improved coupling yields were observed when DMSO was used as the solvent. Products were purified with use of reversed-phase HPLC and, in one case, diastereomeric products (compound 11) were resolved by using this procedure. One of the tripeptidyl nikkomycins behaved as a prodrug but none of the compounds, as measured by in vitro testing, proved more effective than nikkomycin as an anticandidal agent.
• KRAINER, EDUARDO;BECKER, JEFFREY M.;NAIDER, FRED, J. MED. CHEM., 34,(1991) N, C. 174-180
  作者：KRAINER, EDUARDO、BECKER, JEFFREY M.、NAIDER, FRED

  DOI：——

  日期：——
• ANDRUSZKIEWICZ, RYSZARD;CHMARA, HENRYK;MILEWSKI, SLAWOMIR;BOROWSKI, EDWAR+, J. MED. CHEM., 30,(1987) N 10, 1715-1719
  作者：ANDRUSZKIEWICZ, RYSZARD、CHMARA, HENRYK、MILEWSKI, SLAWOMIR、BOROWSKI, EDWAR+

  DOI：——

  日期：——