3,3'-Dimethoxycarbonylpropanoic anhydride | 52944-79-3

• 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: 3,3'-Dimethoxycarbonylpropanoic anhydride
• 英文别名: 3-(methoxycarbonyl)propanoic anhydride；4-methoxy-4-oxobutanoic anhydride；anhydride of monomethyl succinate；monomethyl succinate anhydride；bis-(3-methoxycarbonyl-propionyl)-oxide；Bis-(3-methoxycarbonyl-propionyl)-oxid；4-O-(4-methoxy-4-oxobutanoyl) 1-O-methyl butanedioate
• CAS: 52944-79-3
• 化学式: C₁₀H₁₄O₇
• 分子量: 246.217
• InChiKey: HVJPTZGMOVPTAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,3'-Dimethoxycarbonylpropanoic anhydride 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 生成 乙酰丙酸甲酯
  参考文献：
  名称：

  Benneche, Tore; Christiansen, Mette L.; Undheim, Kjell, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 8, p. 700 - 702

  摘要：

  DOI：
• 作为产物：
  描述：

  丁二酸单甲酯 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 3,3'-Dimethoxycarbonylpropanoic anhydride
  参考文献：
  名称：

  酮亚甲基假肽类似物作为凝血酶抑制剂的合成及其生物学活性。

  摘要：

  酮亚甲基假肽类似物Aa-Pro-Arg psi（COCH2）Gly-pip，其中Aa是D-或L-氨基酸（Dpa，β，β-二苯丙氨酸;αNal，α-萘丙氨酸;βNal，β-萘丙氨酸; Fgl，芴基甘氨酸）具有高度亲脂性的侧链和psi（COCH2）是酮亚甲基假肽键，已通过修饰的Dakin-West反应在非常温和的条件下以高产率使用三肽4直接在其上具有不稳定的官能团合成了高产量侧链。已经进行了对凝血酶抑制的酶促测定。结构-活性关系研究表明，P3位氨基酸的亲脂性侧链对于与凝血酶非极性位点的结合非常重要。在P3位置带有D-Dpa的化合物1a的Ki为0。2 microM，浓度仅高3倍，凝血酶凝血时间就加倍。这些值是相应的D-Phe类似物的约7倍。此外，1a对纤溶酶，Xa因子，尿激酶和激肽释放酶的抑制作用较弱。初步体内试验（3-4千克兔子为动物模型）显示，在1毫克/千克的剂量下，没有可观察到的副作用（血压的变化和血小板在肺中的积聚）。

  DOI：

  10.1021/jm00096a010

文献信息

• Synthesis, characterization, lipophilicity and cytotoxic properties of novel bis(carboxylato)oxalatobis(1-propylamine)platinum(IV) complexes
  作者：Selin Hizal、Michaela Hejl、Michael A. Jakupec、Mathea S. Galanski、Bernhard K. Keppler

  DOI：10.1016/j.ica.2019.03.036

  日期：2019.6

  Abstract A series of novel bis(carboxylato)oxalatobis(1-propylamine)platinum(IV) complexes as well as an ethylamine analog were synthesized. The compounds are either symmetrical with both axial ligands consisting of monoesters of succinic acid, or unsymmetrical, with one axial ligand being acetate. The compounds were characterized in detail by elemental analysis, mass spectrometry and multinuclear

  摘要合成了一系列新型的双（羧基）草酸酯双（1-丙胺）铂（IV）配合物以及乙胺类似物。该化合物与由琥珀酸单酯组成的两个轴向配体对称，或与一个乙酸酯的轴向配体不对称。通过元素分析，质谱和多核（1H，13C，15N，195Pt）NMR光谱对化合物进行详细表征。还原行为通过NMR光谱法进行，而亲脂性通过分析型反相HPLC测量来确定。通过MTT测定评估了抑制人癌细胞系A549（非小细胞肺癌），CH1（PA-1）（卵巢畸胎癌）和SW480（结肠癌）增殖的能力。在最敏感的细胞系CH1（PA-1）中，所有化合物的IC50值均在较低的µM范围内。通常，在两个化合物系列中，IC50值随着亲脂性的增加而降低。然而，用乙酸盐代替琥珀酸酯配体之一对抗增殖活性影响很小，几乎没有不利之处。
• Bis‐ and Tris(carboxylato)platinum(IV) Complexes with Mixed Am(m)ine Ligands in the <i>trans</i> Position Exhibiting Exceptionally High Cytotoxicity
  作者：Björn R. Hoffmeister、Michaela Hejl、Michael A. Jakupec、Mathea Sophia Galanski、Bernhard K. Keppler

  DOI：10.1002/ejic.201403226

  日期：2015.4

  A series of seven diam(m)inebis(carboxylato)dihydroxidoplatinum(IV) and eleven diam(m)inetris(carboxylato)hydroxidoplatinum(IV) complexes with am(m)ine ligands in the trans position was synthesized and characterized by multinuclear 1H, 13C, 15N, 195Pt NMR spectroscopy. IC50 values for all eighteen substances were determined by means of the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide

  合成了一系列具有反位氨基（间）氨酸配体的七个 diam（m）inebis（羧基）二羟基铂（IV）和 11 个 diam（m）inetris（羧基）羟基铂（IV）配合物，并通过多核 1H 表征， 13C、15N、195Pt NMR光谱。所有十八种物质的 IC50 值通过 3-(4,5-二甲基噻唑-2-基)-2,5-二苯基-2H-溴化四唑 (MTT) 测定对三种人类癌细胞系进行测定。在顺铂敏感的 CH1(PA-1) 癌细胞中，diam(m)inebis(carboxylato)dihydroxidoplatinum(IV) 复合物在微摩尔范围内显示出 50% 的抑制浓度，而对于 diam(m)inetris(羧基）氢氧化铂（IV）系列，发现有希望的 IC50 值在纳摩尔范围内。
• Functionalization of carboxylic anhydrides at α-carbon with hypervalent iodine reagents: one-pot conversion of anhydrides to 2-sulfonyloxycarboxylate esters
  作者：Jeffrey M Goff、Michael W Justik、Gerald F Koser

  DOI：10.1016/s0040-4039(01)01028-0

  日期：2001.8

  The treatment of carboxylic anhydrides with iodine(III) sulfonate reagents at ca. 100°C and esterification of the reaction mixtures with MeOH/TsOH·H2O affords 2-sulfonyloxycarboxylate esters. This is consistent with enolic behavior in the anhydrides.

  用碘（III）磺酸盐试剂在约75℃下处理羧酸酐。100℃下，将反应混合物用MeOH / TsOH·H 2 O酯化，得到2-磺酰氧基羧酸酯。这与酸酐中的烯醇行为一致。
• The synthesis and characterization of electron-poor glycosylamines and derived glycosylamides
  作者：Jakub Zýka、Vít Prouza、Nina Habanová、Radek Pohl、Kamil Parkan

  DOI：10.1016/j.carres.2024.109023

  日期：2024.2

  paper describes a unified approach toward diglycosylamines using methanolic ammonia. All the glycosylamines prepared have been fully characterized, and their anomeric configuration has been determined. The article presents a novel method for the N-acylation of diglycosylamines and other electron-poor glycosylamines, which employs nitromethane as a solvent in carboxylic anhydride acylation under acidic conditions

  本文描述了使用甲醇氨制备二糖基胺的统一方法。所有制备的糖基胺都已得到充分表征，并且它们的异头构型已被确定。该文章提出了一种二糖胺和其他缺电子糖胺的N-酰化新方法，该方法使用硝基甲烷作为溶剂在酸性条件下进行羧酸酐酰化。这种转化的可行性体现在广泛的反应底物上。所有糖基酰胺均仅由 β-构型形成。这两个反应构成了合成一类具有N-糖苷键的新型化合物的简单而有效的途径。
• Tetracarboxylatoplatinum(IV) complexes featuring monodentate leaving groups — A rational approach toward exploiting the platinum(IV) prodrug strategy
  作者：Doris Höfer、Hristo P. Varbanov、Anton Legin、Michael A. Jakupec、Alexander Roller、Mathea S. Galanski、Bernhard K. Keppler

  DOI：10.1016/j.jinorgbio.2015.08.018

  日期：2015.12

  A series of novel symmetrically and unsymmetrically coordinated platinum(IV) complexes with monodentate carboxylato ligands was synthesized. The compounds exhibit a general coordination sphere of [Pt(en)(OCOR)(2)(OCOR')(OCOR '')1, where the carboxylato ligands are represented by acetato and succinic acid monoester ligands. Dicarboxylatoplatinum(II) complexes were synthesized and oxidized symmetrically or unsymmetrically to obtain platinum(IV) complexes, which were subsequently carboxylated with noncyclic anhydrides. The compounds were investigated in detail by elemental analysis, mass spectrometry, infrared and multinuclear (H-1,C-13,N-15,Pt-195) NMR spectroscopy as well as by X-ray diffraction in some cases. The reduction behavior was followed by NMR spectroscopy, while stability and lipophilicity were examined by analytical reversed phase HPLC measurements. Cytotoxic properties were studied in three human cancer cell lines derived from cisplatin sensitive ovarian teratocarcinoma (CH1/PA-1), cisplatin insensitive colon carcinoma (SW480) and non-small cell lung cancer (A549). Thereby, the most lipophilic (yet water soluble) platinum(IV) complexes showed promising IC50 values in the low micromolar and even nanomolar range, demonstrating the significant advantage of using equatorially coordinated monodentate carboxylato ligands. (C) 2015 Elsevier Inc. All rights reserved.