2-(3-benzoylthioureido)propanoic acid | 110443-42-0

• 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: 2-(3-benzoylthioureido)propanoic acid
• 英文别名: 2-[(Benzoylcarbamothioyl)amino] propanoic acid；2-(benzoylcarbamothioylamino)propanoic acid
• CAS: 110443-42-0
• 化学式: C₁₁H₁₂N₂O₃S
• 分子量: 252.294
• InChiKey: DYKPOBPEKRSEKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 2-(3-benzoylthioureido)propanoic acid 、 manganese (II) acetate tetrahydrate 以 甲醇 、 水 为溶剂， 以57%的产率得到
  参考文献：
  名称：

  A Novel Manganese(II) Coordination Polymer Built by Thiourea-Based Carboxylate Ligand

  摘要：

  A novel polymer {[Mn(H(2)L)(2)(CH(3)OH)2]center dot H(2)O}n (1) has been prepared by 2-(3-benzoylthioureido)propionic acid (H(3)L) reacting with manganese(II) ion in solution. The crystal structure of the polymer 1 has been characterized by single-crystal x-ray crystallography. The Mn(II) ions in polymer 1 are bridged by mu(2)-mode H(2)L(-) anions, forming an infinite [Mn(H(2)L)(2)(CH(3)OH)(2)](n) chain. Also, the thermostability of the complex 1 has been researched.

  DOI：

  10.1080/15533174.2011.591327
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 水 作用下， 生成 2-(3-benzoylthioureido)propanoic acid
  参考文献：
  名称：

  Toward Efficient Analysis of Mutations in Single Cells from Ethanol-Fixed, Paraffin-Embedded, and Immunohistochemically Stained Tissues

  摘要：

  only a few studies have demonstrated successful molecular analysis after whole genome amplification using single cells dissected from paraffin-embedded tissues. The results in these studies were limited by low-amplification efficiency and high rates of allele dropout. In the present study, the amplification rate using a thoroughly modified primer extension and preamplification-PCR protocol was improved significantly for single cells microdissected from paraffin-embedded and immunohistochemically stained tissues. Tissue fixation with ethanol (85%) and the addition of 0.2 mmol/L EDTA helped to achieve an amplification rate between 67% (segments 200 to 400 bp) and 72% (segments <200 bp). Normal tissue sections were immunohistochemically double stained for overabundance of p53 protein and proliferating cell nuclear antigen. Microdissection of single cells was performed with a manual micromanipulator equipped with a Tungsten needle. Sequence analysis of the TP53 gene was performed after improved primer extension preamplification-PCR and multiplex PCR from single microdissected cells. The rate of allele dropout was at least 68%. These technical advances facilitate routine mutation analysis using a single cell or a few cells microdissected from routinely processed paraffin-embedded normal and tumor tissues. Allele dropout still represents a serious problem in single-cell mutation analysis, especially in samples with limited template DNA and prone to DNA damage.

  DOI：

  10.1038/labinvest.3780437

文献信息

• Ugi reaction of thiouridocarboxylic acids: A synthesis of thiourea-peptoids
  作者：Elnaz Ghasemi、Ashraf S. Shahvelayati、Issa Yavari

  DOI：10.1080/10426507.2015.1085048

  日期：2016.5.3

  Abstract Benzoylthioureidocarboxylic acids, prepared from benzoyl chlorides, potassium thiocyanate, and α-aminoacids, are used as acid components in the Ugi reaction to produce thiourea-peptoids in moderate to good yields. GRAPHICAL ABSTRACT

  摘要 由苯甲酰氯、硫氰酸钾和 α-氨基酸制备的苯甲酰硫脲基羧酸用作 Ugi 反应中的酸组分，以中等至良好的收率生产硫脲类肽。图形概要
• Ionic Liquid as a Green Media for the One-Pot Synthesis of New α- Thiazolodepsipeptide Derivatives via a Four-Component Reaction
  作者：Ashraf S. Shahvelayati、Akram Ashouri、Akram S. Delbari

  DOI：10.2174/1570178613666151112224143

  日期：2016.2.9

  a four-component Condensation/ Passerini tandem reaction of thiourea carboxylic acid derivatives, phenacyl bromides, ketones and isocyanides in 1-methyl-3- pentylimidazolium bromide as new solvent. Results: As shown in Scheme 1, the reaction of thiourea carboxylic acid 1, phenacyl bromide or its derivatives 2, alkyl isocyanides 3 and ketones 4 in an ionic liquid at 50°C produce depsipeptide derivatives

  背景：十肽是在同一含氨基酸的小分子或链中同时具有肽键和酯键的分子。许多二肽显示出非常有前途的生物学活性，包括抗癌，抗菌，抗癌，抗病毒，抗真菌，抗炎，抗凝血或抗致动脉粥样硬化特性。 本文的目的是将离子液体用作绿色介质，通过四组分反应合成新的α-噻唑并二肽肽衍生物。 方法：通过硫脲羧酸衍生物，苯甲酰溴，酮和异氰酸酯的四组分缩合/ Passerini串联反应，在1-甲基-3-戊基咪唑鎓溴化物中作为新溶剂，可轻松一步一步制得含噻唑的二肽。 结果：如方案1所示，在50℃的离子液体中，硫脲羧酸1，苯甲酰溴或其衍生物2，烷基异氰化物3和酮4的反应以良好的产率产生了二肽衍生物5。产物通过1 H NMR，13 C NMR，质谱和IR光谱表征。该反应基于环化反应和Passerini反应的结合而进行。 结论：总而言之，硫脲羧酸，苯甲酰溴或其衍生物，烷基异氰化物和酮在离子液体中在50°C下的反应可产生高产率的二肽
• Anti-Amoebic Properties of Carbonyl Thiourea Derivatives
  作者：Maizatul Ibrahim、Mohd Mohd Yusof、Nakisah Amin

  DOI：10.3390/molecules19045191

  日期：——

  Thiourea derivatives display a broad spectrum of applications in chemistry, various industries, medicines and various other fields. Recently, different thiourea derivatives have been synthesized and explored for their anti-microbial properties. In this study, four carbonyl thiourea derivatives were synthesized and characterized, and then further tested for their anti-amoebic properties on two potential pathogenic species of Acanthamoeba, namely A. castellanii (CCAP 1501/2A) and A. polyphaga (CCAP 1501/3A). The results indicate that these newly-synthesized thiourea derivatives are active against both Acanthamoeba species. The IC50 values obtained were in the range of 2.39–8.77 µg·mL‑1 (9.47–30.46 µM) for A. castellanii and 3.74–9.30 µg·mL‑1 (14.84–31.91 µM) for A. polyphaga. Observations on the amoeba morphology indicated that the compounds caused the reduction of the amoeba size, shortening of their acanthopodia structures, and gave no distinct vacuolar and nuclear structures in the amoeba cells. Meanwhile, fluorescence microscopic observation using acridine orange and propidium iodide (AOPI) staining revealed that the synthesized compounds induced compromised-membrane in the amoeba cells. The results of this study proved that these new carbonyl thiourea derivatives, especially compounds M1 and M2 provide potent cytotoxic properties toward pathogenic Acanthamoeba to suggest that they can be developed as new anti-amoebic agents for the treatment of Acanthamoeba keratitis.

  硫脲衍生物在化学、各种工业、医药和其他领域有着广泛的应用。最近，人们合成了不同的硫脲衍生物，并探索了它们的抗微生物特性。 本研究合成了四种羰基硫脲衍生物并对其进行了表征，然后进一步测试了它们对两种潜在致病性棘阿米巴的抗阿米巴特性，这两种棘阿米巴分别是卡斯特拉氏棘阿米巴（CCAP 1501/2A）和多棘阿米巴（CCAP 1501/3A）。结果表明，这些新合成的硫脲衍生物对这两种棘阿米巴都有活性。卡斯特拉氏阿米巴虫的 IC50 值范围为 2.39-8.77 µg-mL-1 （9.47-30.46 µM），多棘阿米巴虫的 IC50 值范围为 3.74-9.30 µg-mL-1 （14.84-31.91 µM）。对变形虫形态的观察表明，这些化合物导致变形虫体积缩小，棘足结构缩短，并且在变形虫细胞中没有明显的空泡和核结构。同时，利用吖啶橙和碘化丙啶（AOPI）染色进行荧光显微镜观察发现，合成的化合物会导致变形虫细胞膜受损。研究结果表明，这些新的羰基硫脲衍生物，尤其是化合物 M1 和 M2 对致病性阿米巴具有很强的细胞毒性，建议将其开发为治疗阿米巴角膜炎的新型抗阿米巴药剂。
• Synthesis and Characterization of N-benzoyl-N′-carboxyalkyl Substituted Thiourea Derivatives
  作者：Zhonghua Li、Yan Zhang、Yangang Wang

  DOI：10.1080/10426500307952

  日期：2003.2.1

  N-Benzoyl-N'-carboxyl substituted thiourea derivatives (I-X) have been synthesized by the reaction of benzoyl isothiocyanate with amino acids. Their structures are confirmed by IR, (HNMR)-H-1, and elemental analysis. The reaction conditions are experimentally investigated, and the preliminary biological tests show that some of the compounds have excellent plant growth promotion activities.
• Zhang, You-Ming; Wei, Tai-Bao; Wang, Xiu-Chun, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 6, p. 604 - 606
  作者：Zhang, You-Ming、Wei, Tai-Bao、Wang, Xiu-Chun、Yang, Su-You

  DOI：——

  日期：——