monosodium malonate | 2922-55-6

• 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: monosodium malonate
• 英文别名: Malonic acid sodium salt；sodium hydrogen malonate；sodium malonate；malonic acid ; acidic sodium malonate；Malonsaeure; saures Natriummalonat；Malonsaeure; Natriummalonat；sodium;3-hydroxy-3-oxopropanoate
• CAS: 2922-55-6
• 化学式: C₃H₃O₄*Na
• 分子量: 126.044
• InChiKey: LXWZLYDXYCQRJT-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -6.01
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  14-iodo-N-(trifluoroacetyl)daunorubicin 、 monosodium malonate 以 水 、 丙酮 为溶剂， 反应 14.0h， 以84%的产率得到N-(trifluoroacetyl)adriamycin 14-O-hemimalonate
  参考文献：
  名称：

  Adriamycin analogs. Rationale, synthesis, and preliminary antitumor evaluation of highly active DNA-nonbinding N-(trifluoroacetyl)adriamycin 14-O-hemiester derivatives

  摘要：

  N-(Trifluoroacetyl)adriamycin 14-valerate (AD 32), a novel DNA nonbinding analogue of adriamycin with superior experimental antitumor activity, has undergone extensive clinical trial, with documentation of antitumor activity and low toxicity in human subjects. However, poor water solubility necessitates that the drug be administered to patients by continuous intravenous infusion at high dilution in a surfactant-containing formulation, with steroid prophylaxis to protect against a chest pain syndrome associated with the vehicle. On the basis of pharmacologic considerations, the title compounds have been prepared as second-generation analogues of N-(trifluoroacetyl)adriamycin 14-valerate with improved aqueous solubility; use is made of the available carboxylic acid function to solubilize the products in dilute aqueous alkaline medium. Target compounds were made by treating N-(trifluoroacetyl)-14-halodaunorubicin (bromo or iodo) with monosodium salts of dibasic acids (malonic, succinic, glutaric, adipic, pimelic, azelaic, sebacic) in aqueous acetone. All of the products showed significant in vivo antitumor activity against the murine P388 leukemia (ip tumor, ip treatment once daily on days 1, 2, 3, and 4); most compounds were superior to the +181% increase in life span afforded by adriamycin (optimal dose 3.0 mg/kg per day), one of two drugs used as positive controls for the assays. Several of the test compounds showed highly curative activity in this system, similar to N-(trifluoroacetyl)adriamycin 14-valerate, the other positive control agent. The hemiadipate product exhibited the most desirable properties of high antitumor efficacy (86% cure rate all P388 tumor-bearing animals through four levels of a 40-70 mg/kg dose-response range), aqueous solubility (60 mg/mL in pH 7.4 phosphate buffer), and solution stability (no decomposition at 4 degrees C, 0.5% hydrolysis at 27 degrees C, over 24 h at pH 7.4).

  DOI：

  10.1021/jm00147a017

文献信息

• Synthesis, characterization and 1H NMR studies of [Co(en)2(malH)2]ClO4·H2O
  作者：C. Chatterjee、Marie Stephen、Rakesh Kumar、Subroto Das

  DOI：10.1016/s0277-5387(00)84555-6

  日期：1986.1

  chelate ring. The group of the hydrogen malonate ion appeared as a sharp singlet at 2.95 ppm and integration showed the presence of two bimalonate groups. The reactive methylene protons were found to be exchangeable. Ion association by counter ions of the complex ion in DMSO-d6 showed no preference among amino protons. This is as expected for trans complexes with D2h-symmetry.

  的反式- [CO（烯）2（malH）2 ] CLO 4 ·H 2 O的制备由钠氢丙二酸的反应用[CO（烯）复合物2（H 2 ö 2 ]（CLO 4）3在存在高浓度高氯酸根离子，显示出三波段可见光谱（最大γ357、448和542.6 nm），对反式-MA 4 B 2系统进行了诊断，并给出了反式-双乙二胺所预期的特征性IR谱带钴（III）配合物在DMSO-中的1 H NMR光谱d 6揭示了可分配给氨基氢的5.8 ppm宽谱带和螯合环的亚乙基的2.68单个谱带。丙二酸氢根离子的基团在2.95 ppm处显示为尖锐的单峰，并且积分显示存在两个比马龙酸酯基团。发现反应性亚甲基质子是可交换的。DMSO- d 6中复合离子的抗衡离子与离子缔合没有显示出氨基质子之间的偏爱。如具有D 2 h对称性的反式配合物所预期的。
• Spectroscopy of Hydrothermal Reactions. 5. Decarboxylation Kinetics of Malonic Acid and Monosodium Malonate
  作者：P. G. Maiella、T. B. Brill

  DOI：10.1021/jp960397m

  日期：1996.1.1

  The kinetics of decarboxylation of 1.07 m malonic acid and monosodium malonate at 120−230 °C and 275 bar were determined directly in a combined microflow reactor and short-pathlength IR spectroscopy cell. Malonic acid and monosodium malonate decomposed in a single step to CO2 and acetic acid and CO2 and the acetate ion, respectively. The kinetics for malonic acid were modeled as an equilibrium between

  直接在组合微流反应器和短程红外光谱池中测定了1.07 m丙二酸和丙二酸单钠在120-230°C和275 bar下的脱羧动力学。丙二酸和丙二酸单钠在一个步骤中分别分解为CO 2和乙酸，CO 2和乙酸根离子。丙二酸的动力学被建模为丙二酸和单阴离子之间的平衡，并且两种物质平行脱羧。丙二酸单阴离子的Arrhenius参数为E a = 120±2 kJ / mol和ln A（s -1）= 29.4±0.1以及E a = 126±2 kJ / mol和ln A在316不锈钢流动反应器中于120-210°C时丙二酸的（s -1）= 31.4±0.1。单阴离子的脱羧比丙二酸的脱羧慢。在具有金刚石窗口的Pt / Ir合金流动反应器中，丙二酸的脱羧速率在140°C以上比在具有蓝宝石窗口的316不锈钢流动反应器中慢。
• The hydrolysis products of cis-diamminedichloroplatinum(II) 5. The anation kinetics of cis-Pt(X)(NH3)2(OH2)+ (XCl, OH) with glycine, monohydrogen malonate and chloride
  作者：Sian E. Miller、Donald A. House

  DOI：10.1016/s0020-1693(00)90384-0

  日期：1991.9

  mol −1 ; k cy (25.0 °C, pH=4.3, I =1.0 M)=1.03×10 −5 s −1 , Δ H ≠ =88.9 kJ mol −1 , Δ S ≠ =−42 J K −1 mol −1 . The rate ( k 3 , s −1 ) of the chloride release from cis -PtCl(OH)(NH 3 ) 2 to give cis -Pt(OH)NH 3 ) 2 (OH 2 ) + and rate of chloride uptake (k −3 , M −1 s −1 ) have been measured at pH=7.4. Kinetic parameters are k 3 =2.39×10 −5 s −1 (25.0 °C, pH=7.4, I =1.0 M) Δ H ≠ =82.4 kJ mol −1 , Δ S ≠

  摘要用甘氨酸（Nu = gly在pH = 7.4时）或丙二酸氢钠（Nu）对顺式-PtCl（NH 3）2（OH 2）+进行阴离子分光光度法测定的速率常数k obs（s -1） ＝ Hmal-在pH ＝ 4.3时）可以由等式k obs ＝ ko + k Nu [Nu]表示，其中ko是不依赖亲核试剂浓度但取决于pH的水解速率常数，并且k Nu是亲核试剂依赖性路径。 。在Nu = Hmal-的情况下，ko〜0，第一步是单齿配位，由于闭环，第二步（k cy）亲核试剂独立路径。在Nu ＝ gly的情况下，闭环反应足够快以至于与配位同步出现，并且ko是在pH ＝ 7.4时顺式-PtCl（OH）（NH 3）2的碱水解速率常数。与阴离子相关的动力学参数为k Hmal（25.0°C，pH = 4.3，I = 1.0 M）= 9。90×10 -4 M -1 s -1，ΔH≠= 74.8 kJ mol -1，ΔS≠=
• Electroorganic chemistry. XXI. Selective formation of .alpha.-acetoxy ketones and general synthesis of 2,3-disubstituted 2-cyclopentenones through the anodic oxidation of enol acetates
  作者：Tatsuya Shono、Masahisa Okawa、Ikuzo Nishiguchi

  DOI：10.1021/ja00854a030

  日期：1975.10
• Korte,F. et al., Justus Liebigs Annalen der Chemie, 1963, vol. 664, p. 97 - 113
  作者：Korte,F. et al.

  DOI：——

  日期：——