3-(3,4-dichlorophenylthio)propanoic acid | 66892-35-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(3,4-dichlorophenylthio)propanoic acid
• 英文别名: 3-(3,4-Dichlorophenyl)sulfanylpropanoic acid
• CAS: 66892-35-1
• 化学式: C₉H₈Cl₂O₂S
• 分子量: 251.133
• InChiKey: MZCHHMVVXHZGAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3,4-dichlorophenylthio)propanoic acid 在 硫酸 、 溴 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 反应 41.0h， 生成 7,8-dichloro-2-hydrazineyl-4H-thiochromeno[4,3-d]thiazole
  参考文献：
  名称：

  Synthesis of Rigidified eIF4E/eIF4G Inhibitor-1 (4EGI-1) Mimetic and Their in Vitro Characterization as Inhibitors of Protein–Protein Interaction

  摘要：

  The 4EGI-1 is the prototypic inhibitor of eIF4E/eIF4G interaction, a potent inhibitor of translation initiation in vitro and in vivo and an efficacious anticancer agent in animal models of human cancers. We report on the design, synthesis, and in vitro characterization of a series of rigidified mimetic of this prototypic inhibitor in which the phenyl in the 2-(4-(3,4-dichlorophenyl)thiazol-2-yl) moiety was bridged into a tricyclic system. The bridge consisted one of the following: ethylene, methylene oxide, methylenesulfide, methylenesulfoxide, and methylenesulfone. Numerous analogues in this series were found to be markedly more potent than the parent prototypic inhibitor in the inhibition of eIF4E/eIF4G interaction, thus preventing the eIF4F complex formation, a rate limiting step in the translation initiation cascade in eukaryotes, and in inhibition of human cancer cell proliferation.

  DOI：

  10.1021/jm401733v
• 作为产物：
  描述：

  3-氯丙酸 、 3,4-二氯苯硫酚 在 potassium hydroxide 作用下， 反应 0.17h， 生成 3-(3,4-dichlorophenylthio)propanoic acid
  参考文献：
  名称：

  Synthesis and Antifungal Activity of Some Thiazole Derivatives

  摘要：

  一系列噻唑衍生物的设计与合成得以实现。新型合成化合物的结构通过高分辨质谱（HRMS）、核磁共振氢谱（1H NMR）和碳谱（13C NMR）进行了表征。合成的化合物分别通过琼脂杯平板法和小体积滴定法在体外对十种真菌进行了评估。抗真菌筛选结果显示，在所有筛选的化合物中，有三项展现出中等抗真菌活性。化合物3h对抗两种真菌株C. neoformans和C. albicas的最小抑制浓度（MIC）值分别为8 μg mL-1。化合物3i对抗C. neoformans和T. mentagrophytes的MIC值分别为8 μg mL-1和16 μg mL-1，而3a对抗T. mentagrophytes的MIC值为16 μg mL-1，其余化合物的MIC值均超过32 μg mL-1。

  DOI：

  10.14233/ajchem.2013.13185

文献信息

• Design and Synthesis of α,β-Epoxyketones as New Anticancer Agents
  作者：Zhengyue Ma、Xinghua Zhang、Shikui Wang、Yang He、Gengliang Yang、Beilei Li、Junjie Yang、Yuejuan Lu、Jiewei Sun

  DOI：10.1002/cjoc.201190153

  日期：2011.4

  As epoxy functional group has high anticancer activity, α,β‐epoxyketones were designed and synthesized as new anticancer agents, and their structures were confirmed by UV, 1H NMR, IR, MS technigeces and elemental analysis. Their in vitro anticancer activities were evaluated by MTT method and the results showed that the compound 4c exhibited good activity with IC50 of 17.8, 22.0 and 24.1 µg/mL against

  由于环氧官能团具有较高的抗癌活性，因此设计并合成了α，β-环氧酮作为新型抗癌剂，并通过UV，1 H NMR，IR，MS技术和元素分析确定了它们的结构。用MTT法评估了它们的体外抗癌活性，结果表明化合物4c对A-549，Hela和HepG2细胞的IC 50表现出良好的活性，IC 50分别为17.8、22.0和24.1 µg / mL。通过胃内给药的小鼠的LD50剂量为1864.4mg / kg。因此，α，β-环氧酮可能会提供新的抗癌药。
• Spiro-imidazolones for alleviating diabetes-associated conditions, processes for preparing them, and pharmaceutical compositions containing them
  申请人：PFIZER INC.

  公开号：EP0028485A1

  公开（公告）日：1981-05-13

  Spiro-imidazolones, useful for alleviating diabetes-associated conditions such as diabetic cataracts, retinopathy and neuropathy, of the formula:-H N and the pharmaceutically acceptable acid addition salts thereof, wherein W is -(CH2)n-; X is hydrogen and X is hydrogen, fluorine, chlorine, bromine, C1-C4 alkyl or C1-C4 alkoxy; or X and X1, when taken separately, are each chlorine, C1-C4 alkyl or C1-C4 alkoxy, and when taken together are -OCH2(CH2)nO-; Y is W, oxygen, sulfur, oxosulfur or dioxosulfur; and each n is independently zero or one; pharmaceutical compositions containing them, and processes for their preparation.

  用于缓解糖尿病相关病症（如糖尿病性白内障、视网膜病变和神经病变）的螺咪唑啉酮，其式为：-H N 及其药学上可接受的酸加成盐，其中 W 是-(CH2)n-； X 是氢，X 是氢、氟、氯、溴、C1-C4 烷基或 C1-C4 烷氧基；或 X 和 X1 分别为氯、C1-C4 烷基或 C1-C4 烷氧基，合在一起为-OCH2(CH2)nO-； Y 是 W、氧、硫、氧硫或二氧硫；每个 n 独立地为 0 或 1；含有它们的药物组合物及其制备工艺。
• SARGES, R.
  作者：SARGES, R.

  DOI：——

  日期：——
• US4053480A
  申请人：——

  公开号：US4053480A

  公开（公告）日：1977-10-11
• US4086240A
  申请人：——

  公开号：US4086240A

  公开（公告）日：1978-04-25