1-苯甲酰基-3-(2-羟基苯基)硫脲 | 53514-41-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-苯甲酰基-3-(2-羟基苯基)硫脲
• 英文名称: N-benzoyl-N'-(o-hydroxyphenyl)thiourea
• 英文别名: N-benzoyl-N'-(2-hydroxyphenyl)thiocarbamide；N-benzoyl-N′-(o-hydroxyphenyl)thiourea；N-[(2-hydroxyphenyl)carbamothioyl]benzamide；N-(2-hydroxyphenyl)-N'-benzoylthiourea；N-Benzoyl-N'-(2-hydroxy-phenyl)-thioharnstoff；N-benzoyl-N'-(2-hydroxy-phenyl)-thiourea；N-[[(2-hydroxyphenyl)amino]thioxomethyl]benzamide；N-benzoyl N’-2-hydroxyphenylthiourea；3-benzoyl-1-(2-hydroxyphenyl)thiourea；1-Benzoyl-3-(2-hydroxyphenyl)thiourea
• CAS: 53514-41-3
• 化学式: C₁₄H₁₂N₂O₂S
• 分子量: 272.327
• InChiKey: RCKKAMQNVBUTBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.4
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2930909090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Benzoyl-3-(2-hydroxyphenyl)thiourea
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 1-Benzoyl-3-(2-hydroxyphenyl)thiourea
CAS number: 53514-41-3

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C14H12N2O2S
Molecular weight: 272.3

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, sulfur oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1-苯甲酰基-3-(2-羟基苯基)硫脲 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 生成 邻羟基苯基硫脲
  参考文献：
  名称：

  设计，合成和评估2-氨基噻唑衍生物作为鞘氨醇激酶抑制剂

  摘要：

  鞘氨醇激酶（SphK1，SphK2）是鞘氨醇-1-磷酸酯（S1P）的主要调节剂，鞘氨醇-1-磷酸酯是一种参与多种生理和病理生理功能的多效脂质介体。SphK是新型抗癌和抗炎剂的靶标，这些抗癌剂和抗炎剂可促进细胞凋亡并调节自身免疫性疾病。本文中，我们描述了氨基噻唑类SphK抑制剂的设计，合成和评估。通过使用已知的SKI-II支架进行一系列修饰来定义结构-活性关系，已经发现了有效的抑制剂。我们确定了N-（4-甲基噻唑-2-基）-（2,4'-bithiazol）-2'-胺（24，ST-1803 ; IC 50 值：7.3μM（SphK1），6.5μM（SphK2））有望成为进一步体内研究和结构开发的有希望的候选者。

  DOI：

  10.1016/j.bmc.2014.07.044
• 作为产物：
  描述：

  苯甲酰氯 以 丙酮 为溶剂， 反应 0.75h， 生成 1-苯甲酰基-3-(2-羟基苯基)硫脲
  参考文献：
  名称：

  设计，合成和评估2-氨基噻唑衍生物作为鞘氨醇激酶抑制剂

  摘要：

  鞘氨醇激酶（SphK1，SphK2）是鞘氨醇-1-磷酸酯（S1P）的主要调节剂，鞘氨醇-1-磷酸酯是一种参与多种生理和病理生理功能的多效脂质介体。SphK是新型抗癌和抗炎剂的靶标，这些抗癌剂和抗炎剂可促进细胞凋亡并调节自身免疫性疾病。本文中，我们描述了氨基噻唑类SphK抑制剂的设计，合成和评估。通过使用已知的SKI-II支架进行一系列修饰来定义结构-活性关系，已经发现了有效的抑制剂。我们确定了N-（4-甲基噻唑-2-基）-（2,4'-bithiazol）-2'-胺（24，ST-1803 ; IC 50 值：7.3μM（SphK1），6.5μM（SphK2））有望成为进一步体内研究和结构开发的有希望的候选者。

  DOI：

  10.1016/j.bmc.2014.07.044

文献信息

• Synthesis and biological evaluation of 3-amino-1,2,4-triazole derivatives as potential anticancer compounds
  作者：Oleksandr Grytsai、Oksana Valiashko、Manon Penco-Campillo、Maeva Dufies、Anais Hagege、Luc Demange、Sonia Martial、Gilles Pagès、Cyril Ronco、Rachid Benhida

  DOI：10.1016/j.bioorg.2020.104271

  日期：2020.11

  Two series of compounds carrying 3-amino-1,2,4-triazole scaffold were synthesized and evaluated for their anticancer activity against a panel of cancer cell lines using XTT assay. The 1,2,4-triazole synthesis was revisited for the first series of pyridyl derivatives. The biological results revealed the efficiency of the 3-amino-1,2,4-triazole core that could not be replaced and a clear beneficial effect

  合成了携带3-氨基-1,2,4-三唑支架的两个系列的化合物，并使用XTT分析评估了它们对一组癌细胞系的抗癌活性。重新讨论了第一批吡啶基衍生物的1,2,4-三唑合成。生物学结果表明，对于这两个系列，不能替代的3-氨基-1,2,4-三唑核的有效性以及在三唑的3位的3-溴苯基氨基部分具有明显的有益作用（化合物2.6和4.6）在多个测试的细胞系上。此外，我们的结果指出了这些化合物的抗血管生成活性。总体而言，5-芳基-3-苯基氨基-1,2,4-三唑结构具有有前途的双重抗癌活性。
• OPIOID RECEPTOR MODULATORS AND USE THEREOF
  申请人：National Health Research Institutes

  公开号：US20170056377A1

  公开（公告）日：2017-03-02

  Disclosed is an in vitro screening method for identifying an antagonist-to-agonist allosteric modifier of a mu-opioid receptor and an in vivo method for confirming that a test compound is such a modifier of a mu-opioid receptor. Also disclosed is a method for treating an opioid receptor-associated condition using a compound of Formula (I) and a pharmaceutical composition containing the same.

  揭示了一种体外筛选方法，用于识别μ-阿片受体的拮抗剂-激动剂异位调节剂，并揭示了一种体内方法，用于确认测试化合物是否为μ-阿片受体的这种调节剂。还揭示了一种使用式（I）化合物和含有该化合物的药物组合物治疗阿片受体相关疾病的方法。
• Ultrasound promoted synthesis, characterization and computational studies of some thiourea derivatives
  作者：Felix Odame、Eric C. Hosten、Kevin Lobb、Zenixole Tshentu

  DOI：10.1016/j.molstruc.2020.128302

  日期：2020.9

  Abstract Synthesis of some thiourea derivatives have been achieved by using ultrasound, the compounds have been characterised using IR, NMR, GC-MS and elemental analysis. The single crystal X-ray structure of N-[(benzyloxy)methanethioyl]benzamide (IV), 1-benzoyl-3-(2-hydroxyethyl)thiourea (V) and 3-benzoyl-1-(1-benzylpiperidin-4-yl)thiourea (VI) has been presented and the bond lengths and bond angles

  摘要 利用超声波合成了一些硫脲衍生物，并用红外、核磁共振、气相色谱-质谱和元素分析对化合物进行了表征。N-[(苄氧基)甲硫酰基]苯甲酰胺(IV)、1-苯甲酰基-3-(2-羟乙基)硫脲(V)和3-苯甲酰基-1-(1-苄基哌啶-4-)的单晶X射线结构基) 硫脲 (VI) 已被提出，键长和键角与计算结果形成对比。还计算和讨论了 HOMO 和 LUMO 能级以及化合物的全局化学反应性描述符。在分子静电势和振动频率计算中获得了化合物 IV 至 VI 的两种共轭体，并且已经讨论了这些。
• N-取代芳基(芳甲酰氨基)-N′-取代芳甲酰基 硫脲类化合物在蓝藻生长抑制中的应用
  申请人：华中师范大学

  公开号：CN107041374B

  公开（公告）日：2020-05-05

  本发明涉及N‑取代芳基(芳甲酰氨基)‑N'‑取代芳甲酰基硫脲类化合物在蓝藻生长抑制中的应用。本发明提供的具有通式ⅠN‑取代芳基‑N'‑取代芳甲酰基硫脲类化合物以及通式Ⅱ所述N‑取代芳甲酰氨基‑N'‑取代芳甲酰基硫脲类化合物对蓝藻果糖‑1,6‑二磷酸醛缩酶具有较好的抑制效果，可用于蓝藻果糖‑1,6‑二磷酸醛缩酶活性的抑制。蓝藻果糖‑1,6‑二磷酸醛缩酶酶体实验表明：此类化合物对蓝藻果糖‑1,6‑二磷酸醛缩酶有较好的抑制效果。通式I所示的结构为：通式Ⅰ，通式Ⅱ所示的结构为：通式Ⅱ。
• Design, synthesis and algicides activities of thiourea derivatives as the novel scaffold aldolase inhibitors
  作者：Shan Xiao、Lin Wei、Zongqin Hong、Li Rao、Yanliang Ren、Jian Wan、Lingling Feng

  DOI：10.1016/j.bmc.2019.01.023

  日期：2019.3

  further elucidated by jointly using DOX computational protocol, MM-PBSA and site-directed mutagenesis assays. The positive results suggest that strategy adopted in this study was promising to rapidly discovery the potent inhibitors with novel scaffolds. The satisfactory algicide activities suggest that the thiourea derivatives is very likely to be a promising lead for the development of novel specific

  通过使用新的基于片段的虚拟筛选策略，从果蓝藻（CyFBA）的果糖-1、6-二磷酸醛缩酶的活性位点重新发现了两个系列的新型FBA-II抑制剂（硫脲衍生物）。相比之下，与N-（苯基氨基甲硫酰基）苯甲酰胺衍生物（L1-L13）相比，大多数N-（2-苯甲酰基肼-1-碳硫基）苯甲酰胺衍生物（L14〜L22）显示出更高的CyFBA-II抑制活性。尤其是，化合物L14不仅显示出较高的CyFBA-II活性（Ki = 0.65μM），而且还显示出最有效的针对拟球藻sp。的体内活性。PCC 6803（EC50 = 0.09 ppm），比以前的抑制剂（EC50 = 0.6 ppm）高（7倍）。通过联合使用DOX计算方案，MM-PBSA和定点诱变分析进一步阐明了化合物L14和CyFBA-II的结合模式。积极的结果表明，这项研究中采用的策略有望迅速发现具有新型支架的有效抑制剂。令人满意的除藻剂活性表明，硫脲衍生物很