iodomethyl butanoate | 63379-59-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: iodomethyl butanoate
• 英文别名: iodomethyl butyrate
• CAS: 63379-59-9
• 化学式: C₅H₉IO₂
• 分子量: 228.03
• InChiKey: AIEFWPONAXOMOR-UHFFFAOYSA-N

物化性质

• 沸点：
  194.3±23.0 °C(Predicted)
• 密度：
  1.709±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  iodomethyl butanoate 在 Amberlite IRA-400 Cl(-) exchange resin 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 1-<(butanoyloxy)methyl>-2-<(hydroxyimino)methyl>-3-methylimidazolium chloride
  参考文献：
  名称：

  Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 2. Preparation and in vitro and in vivo evaluaton of 1-(alkoxymethyl)-2-[(hydroxyimino)methyl]-3-methylimidazolium halides for reactivation of organophosphorus-inhibited acetylcholinesterases

  摘要：

  A series of structurally related mono- and bis-1,3-disubstituted 2-[(hydroxyimino)methyl]imidazolium halides were evaluated in vitro for their ability to reactivate electric eel, bovine, and human erythrocyte (RBC) acetylcholinesterases (AChE) inhibited by ethyl p-nitrophenyl methylphosphonate (EPMP) and 3,3-dimethyl-2-butyl methyl-phosphonofluoridate (soman, GD). All new compounds were characterized for (hydroxyimino)methyl acid dissociation constant, nucleophilicity, octanol-buffer partition coefficient, reversible AChE inhibition, and kinetics of reactivation of EPMP-inhibited AChEs. For GD-inhibited AChEs, maximal reactivation was used to compare compounds since rapid phosphonyl enzyme dealkylation "aging" complicated interpretation of kinetic constants. For comparison, we also evaluated three known pyridinium therapeutics, 2-PAM, HI-6, and toxogonin. In vivo evaluation in mice revealed that when selected imidazolium compounds were coadministered with atropine sulfate, they were effective in providing lifesaving protection against both GD and EPMP challenges. This was a major accomplishment in the search for effective anticholinesterase therapeutics--the synthesis and preliminary evaluation of the first new monoquaternary soman antidotes with potencies superior to 2-PAM. Significantly, there was an apparent inverse relationship between in vitro and in vivo results; the most potent in vivo compounds proved to be the poorest in vitro reactivators. These results suggested that an alternative and possibly novel antidotal mechanism of protective action may be applicable for the imidazolium aldoximes. Selected compounds were also evaluated for their inhibition of AChE phosphorylation by GD and antimuscarinic and antinicotinic receptor blocking effects.

  DOI：

  10.1021/jm00122a034
• 作为产物：
  描述：

  丁酸氯甲酯 在 sodium iodide 作用下， 以 丙酮 为溶剂， 生成 iodomethyl butanoate
  参考文献：
  名称：

  Compositions and methods for enhanced drug delivery

  摘要：

  本发明涉及将药物制剂传递到患者的膜层，包括皮肤层或黏膜膜层的方法。药物制剂与化学修饰剂通过生理可切割键共价结合，从而增强了药物的膜传输和传递。

  公开号：

  US05607691A1

文献信息

• [EN] GLUCOKINASE ACTIVATORS AND METHODS OF USING SAME<br/>[FR] ACTIVATEURS DE GLUCOKINASE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2018017910A1

  公开（公告）日：2018-01-25

  A compound, enantiomer, prodrug, diastereomer, or salt is provided which is an activator of the enzyme glucokinase and thus is believed to be useful in treating diabetes and related diseases, which compound has the structure (I). A method for treating diabetes and related disease employing the compound, enantiomer, prodrug, diastereomer, or salt is also provided.

  提供一种化合物、对映体、前药、二对映体或盐，该化合物是葡萄糖激酶的激活剂，因此被认为在治疗糖尿病及相关疾病方面是有用的，该化合物具有结构（I）。还提供了一种利用该化合物、对映体、前药、二对映体或盐治疗糖尿病及相关疾病的方法。
• New Sugar‐Based Permeant Analogs of D‐ Myo ‐Inositol 1,4,5‐Trisphosphate Mimicking the Effect of Vasopressin: Synthesis and Biologic Evaluation*
  作者：Françoise Chrétien、Fabien Roussel、Mauricette Hilly、Jean‐Pierre Mauger、Yves Chapleur

  DOI：10.1081/car-200068070

  日期：2005.8.1

  of the xylose‐inositol analogy, a series of permeant analogs of D‐myo‐inositol 1,4,5‐trisphosphate (InsP3) have been synthesized by various esterifications of the phosphate groups. Their ability to cross the cell membrane has been tested on vasopressin cells. Very fast liberation of calcium occurs when active analogs are introduced in the extracellular medium on intact cells. Membrane crossing as well

  根据木糖-肌醇的类似物，已通过磷酸酯基团的各种酯化反应合成了一系列D-肌醇1,4,5-三磷酸酯（InsP3）的渗透性类似物。在血管加压素细胞上已经测试了它们穿过细胞膜的能力。当将活性类似物引入完整细胞的细胞外培养基中时，钙会非常快速地释放出来。使用所有磷酸酯基团的酰氧基甲基酯化，膜的转运以及磷酸酯的水解都非常快。游离化合物在细胞中的行为类似于InsP3。对于表达血管加压素受体的大鼠肝细胞，以这种方式制备的一种类似物的行为类似于血管加压素。*致敬Jacques H. van Boom及其在该领域的杰出贡献。
• Reaction of alkylcarbonyloxymethyl halides with phenols: reevaluating the influence of steric hindrance
  作者：Joshua D. Thomas、Kenneth B. Sloan

  DOI：10.1016/j.tetlet.2006.09.118

  日期：2006.12

  Evidence is presented that contradicts an earlier finding that, in the absence of steric hindrance, the coupling reaction of alkylcarbonyloxymethyl (ACOM) halides with phenols favors acylated product. A one-step synthesis is used to generate sterically unhindered ACOM iodides, which are then reacted with several phenols to give mainly alkylated phenol.

  提出的证据与较早的发现相反，在没有空间位阻的情况下，烷基羰基氧基甲基（ACOM）卤化物与酚类的偶联反应有利于酰化产物。一步合成用于生成空间不受阻碍的ACOM碘化物，然后使其与几种酚反应，主要生成烷基化苯酚。
• Reaction of α-(<i>n</i>-Alkylcarbonyloxy)alkyl (ACOA) Halides with 4-Hydroxy­acetanilide and 2,2,5,7,8-Pentamethyl-6-chromanol: The Effect of Steric Hindrance­ on Reaction Path
  作者：Kenneth Sloan、Joshua Thomas

  DOI：10.1055/s-2007-1000858

  日期：2008.1

  A convenient synthesis of α-( N-alkylcarbonyloxy)alkyl (ACOA) iodides has been developed and a homologous series of N-alkylcarbonyloxymethyl (ACOM) iodides have been used to alkylate 4-hydroxyacetanilide (acetaminophen, APAP), a sterically unhindered phenol, and a sterically hindered phenol (2,2,5,7,8-pentamethyl-6-chromanol). Steric hindrance was not a significant factor in the ratio of acylated (Path

  已经开发了一种方便合成 α-(N-烷基羰基氧基)烷基 (ACOA) 碘化物的方法，并且已经使用同源系列的 N-烷基羰基氧基甲基 (ACOM) 碘化物来烷基化 4-羟基乙酰苯胺（对乙酰氨基酚，APAP），一种空间位阻不受阻碍的苯酚，和位阻酚（2,2,5,7,8-pentamethyl-6-chromanol）。对于这些反应，空间位阻不是酰化（路径 b）与烷基化（路径 a）的比率的重要因素。鉴于已报道的与空间位阻 ACOM 前药相关的毒性，N-烷基 ACOM 和 ACOA 前体本身作为更常用的基于新戊酸盐的衍生物的可行替代品。
• Retinoyloxy (substituted) methyl butyrates useful for the treatment of
  申请人：Bar-Ilan University

  公开号：US05710176A1

  公开（公告）日：1998-01-20

  This invention relates to the novel compounds of Formula (I) and pharmaceutical compositions containing same, to methods of treating, preventing or ameliorating cancer and other proliferative diseases in a subject in need of such treatment comprising administering a compound of Formula (I) and pharmaceutically acceptable salts and prodrugs thereof. ##STR1##

  这项发明涉及到公式(I)的新化合物以及含有这些化合物的药物组合物，以及治疗、预防或改善患有癌症和其他增殖性疾病的受试者的方法，包括给予公式(I)的化合物及其药用盐和前药。