2-(3-(甲硫基)丙基)异吲哚啉-1,3-二酮 | 52096-79-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: 2-(3-(甲硫基)丙基)异吲哚啉-1,3-二酮
• 英文名称: methyl 3-(N-phthalylamino)propyl sulfide
• 英文别名: methyl 3-phthalimidopropyl sulfide；2-<2-(Methylthio)propyl>-1H-isoindole-1,3(2H)-dione；N-(3-(methylthio)propyl)phthalimide；N-methylthiopropyl phthalimide；N-(3-methylsulfanyl-propyl)-phthalimide；N-(3-Methylmercapto-propyl)-phthalimid；2-(3-(Methylthio)propyl)isoindoline-1,3-dione；2-(3-methylsulfanylpropyl)isoindole-1,3-dione
• CAS: 52096-79-4
• 化学式: C₁₂H₁₃NO₂S
• mdl: MFCD23135288
• 分子量: 235.307
• InChiKey: VOMKYOKPFWVCME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  2-(3-(甲硫基)丙基)异吲哚啉-1,3-二酮 在 肼 作用下， 生成 3-(甲基三)丙烯酸呋喃
  参考文献：
  名称：

  有机硫化物的生物转化。第7部分。通过微生物生物转化形成手性异硫氰酸根合亚砜和相关化合物

  摘要：

  真菌Helminthosporium种类NRRL 4671和伊莎贝拉莫氏菌ATCC 42613已用于一系列异硫氰酸根合烷基甲基硫化物及其合成前体ω-（甲硫基）烷基邻苯二甲酰亚胺的生物转化。^ h。在所有情况下，这些物种主要产生（S）亚砜；伊萨贝利纳霉（M. isabellina）得到（R）异硫氰酸根合烷基甲基亚砜，但在两个ω-（甲硫基）烷基邻苯二甲酰亚胺的情况下，亚砜基本转化为砜，导致前者以（S）构型分离。对先前报道的两种生物转化产物的结构进行了更正（Tetrahedron：不对称，1994年，5，1129）。

  DOI：

  10.1016/0957-4166(95)00200-9
• 作为产物：
  描述：

  3-氯丙基-甲基硫醚 、 potassium phtalimide 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以96.1%的产率得到2-(3-(甲硫基)丙基)异吲哚啉-1,3-二酮
  参考文献：
  名称：

  一种制备3-甲硫基丙胺的方法

  摘要：

  本发明提供了一种3‑甲硫基丙胺的制备方法，其特征是在微波和超声波的作用下，以国内易得的食用香料3‑甲硫基丙醇为起始原料，反应时间短，总产率较高。在微波和超声波的作用下，首先3‑甲硫基丙醇与氯化亚砜在回流的条件下反应20‑60min制得3‑甲硫基‑1‑氯丙烷，产率大于95％；然后在80‑90℃下3‑甲硫基‑1‑氯丙烷与邻苯二甲酰亚胺钾反应0.5‑2.5h制得N‑3‑甲硫基丙基邻苯二甲酰亚胺，产率大于94％；最后N‑3‑甲硫基丙基邻苯二甲酰亚胺与水合肼在无水乙醇中回流反应20‑60min制得3‑甲硫基丙胺，产率大于85％。

  公开号：

  CN107778205B

文献信息

• Nucleoside Analogs. 14. The Synthesis and Antitumor Activity in Mice of Molecular Combinations of 5-Fluorouracil and <i>N</i>-(2-Chloroethyl)-<i>N</i>-nitrosourea Moieties Separated by a Three-Carbon Chain
  作者：R. Stanley McElhinney、Joan E. McCormick、Mike C. Bibby、John A. Double、Marco Radacic、Patrick Dumont

  DOI：10.1021/jm9507237

  日期：1996.1.1

  5-fluorouracil (5-FU) seco-nucleosdies having as the "sugar" moiety a two-carbon (C2) side chain carrying a N-(2-chloroethyl)-N-nitrosourea group were designed as molecular combinations of antimetabolite and alkylating agent, but hydrolytic release of free 5-FU was not fast enough for significant contribution to the high activity they showed against colon and breast tumors in mice. In the present study

  将具有N-（2-氯乙基）-N-亚硝基脲基团的两个碳（C2）侧链作为“糖”部分的5-氟尿嘧啶（5-FU）核糖核酸被设计为抗代谢物和烷基化的分子组合但是，游离5-FU的水解释放速度还不够快，不足以显着提高它们对小鼠结肠和乳腺肿瘤表现出的高活性。在目前对反应性更高的C3核糖核苷的合成的研究中，发现通过标准方法可以方便地获得烷氧基/尿嘧啶-1-基类型的烷氧基/尿嘧啶-1-基类型，这些基团连接到前体邻苯二甲酰亚胺的醛中心。 。甲硫基/尿嘧啶-1-基类似物需要相对大量的甲硫醇试剂，对烷基甲基硫醚的α-氯化或其S-氧化物的Pummerer重排，或异硫脲溴化铵的连续水解和甲基化的替代方案的研究令人失望。为了成功制备烷氧基/尿嘧啶-3-基化合物，用于C2同源物的途径需要进行大量的实验修饰。除了这些O，N-和S，N-乙缩醛以外，还制备了带有两个5-F​​U残基的一些N，N-乙缩醛。新药物已经针对小鼠实验性肿瘤
• �ber Homologe des Sulforaphans und �ber ?-Aminoalkyl-sulfoxyde
  作者：P. Karrer、E. Scheitlin、H. Siegrist

  DOI：10.1002/hlca.19500330516

  日期：——

  Es wurden höhere und niedrigere Homologe des Sulforaphans in racemischer und in optisch aktiven Formen hergestellt. Die synthetisierten Verbindungen sind folgende:

  已经以外消旋和旋光形式制备了萝卜硫烷的较高和较低的同系物。合成的化合物如下：
• Phosphoinositide 3-kinase inhibitor compounds and methods of use
  申请人：Folkes Adrian

  公开号：US20080039459A1

  公开（公告）日：2008-02-14

  Compounds of Formulas Ia and Ib, and including stereoisomers, geometric isomers, tautomers, solvates, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting lipid kinases including PI3K, and for treating disorders such as cancer mediated by lipid kinases. Methods of using compounds of Formula Ia and Ib for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

  公式Ia和Ib的化合物，包括立体异构体，几何异构体，互变异构体，溶剂化物，代谢物和其药学上可接受的盐，可用于抑制脂质激酶包括PI3K，并用于治疗由脂质激酶介导的癌症等疾病。公开了使用公式Ia和Ib的化合物用于哺乳动物细胞中的体外，体内和原位诊断，预防或治疗此类疾病或相关病理条件的方法。
• PHOSPHOINOSITIDE 3-KINASE INHIBITOR COMPOUNDS AND METHODS OF USE
  申请人：Castanedo Georgette

  公开号：US20110105464A1

  公开（公告）日：2011-05-05

  Methods of using compounds of Formula Ia and Ib for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

  本文披露了使用Ia和Ib化合物的方法，用于哺乳动物细胞中的体外、体内和原位诊断、预防或治疗相关病理状况。
• Synthesis of Novel Analogs of Acetyl Coenzyme A: Mimics of Enzyme Reaction Intermediates
  作者：David P. Martin、Richard T. Bibart、Dale G. Drueckhammer

  DOI：10.1021/ja00090a014

  日期：1994.6

  An improved method for the synthesis of analogs of coenzyme A (CoA) and its thioesters, which are modified in the thiol or thioester moiety, has been developed using a combination of chemical and enzymatic reactions, The enzymes catalyzing the last two steps of CoA biosynthesis were used to prepare a CoA analog (1c) in which an amide bond is replaced by a thioester bond and the thiol group is replaced by a methyl group. Reaction of 1c with a primary amine in aqueous solution results in aminolysis of the thioester linkage to form the desired CoA analog. Reaction with different amines permits the introduction of a variety of functional groups in place of the nor mal thiol or thioester group. This methodology has been used in the synthesis of five new analogs of acetyl-CoA in which the thioester sulfur is replaced by a methylene group and the acetyl group is replaced by carboxylate (14a), nitro (14b), carboxamide (14c), methyl sulfoxide (14d), and methyl sulfone (14e) groups. 14a-c were designed to mimic the possible enolate or enol intermediate in the reaction of citrate synthase and related enzymes. 14a and 14c are potent inhibitors of citrate synthase, with K-i values 1000- and 570-fold lower than the K-m for acetyl-CoA, respectively. CD titrations indicate that 14a and 14c have low affinity for citrate synthase in the absence of oxaloacetate, consistent with their recognition as enol or enolate analogs. 14b is a poor inhibitor of citrate synthase, with affinity slightly lower than that for acetyl-CoA. These results are consistent with generation of the enol form of acetyl-CoA as the nucleophilic intermediate in the reaction of citrate synthase. 14d and 14e were designed to mimic the tetrahedral intermediate or transition state in the reaction of chloramphenicol acetyltransferase and related acetyl-CoA-dependent acetyltransferases. Both compounds are poor inhibitors of chloramphenicol acetyltransferase, with affinities slightly lower than that of acetyl-CoA, indicating that these compounds are not good mimics of the enzyme-bound tetrahedral intermediate or transition state.