4-(4-氧代-2-硫代氧基-3-噻唑基)丁酸 | 18623-60-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 4-(4-氧代-2-硫代氧基-3-噻唑基)丁酸
• 中文别名: 4-(4-氧代-2-硫代-四氢噻唑-3-基)丁酸；4-(4-氧代-2-硫基亚甲基-1,3-四氢噻唑-3-基)丁酸；4-(4-氧代-2-硫代-3-四氢噻唑基)丁酸；4-(4-氧代-2-硫代-1,3-四氢噻唑-3-基)丁酸
• 英文名称: 4-oxo-2-thioxo-3-thiazolidinebutanoic acid
• 英文别名: 4-(4-oxo-2-thioxo-1,3-thiazolidin-3-yl)butanoic acid；rhodanine-3-butyric acid；3-(3‘-hydroxycarbonylpropyl)-2-thioxothiazolidin-4-one；4-(4-oxo-2-thioxothiazolidin-3-yl)butyric acid；4-(4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)butanoic acid；4-(4-Oxo-2-thioxo-thiazolidin-3-yl)-butyric acid
• CAS: 18623-60-4
• 化学式: C₇H₉NO₃S₂
• mdl: MFCD00457540
• 分子量: 219.285
• InChiKey: KCDHBLVYRSYUBV-UHFFFAOYSA-N

物化性质

• 熔点：
  118-119 °C
• 沸点：
  405.5±47.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-(4-Oxo-2-thioxo-thiazolidin-3-yl)-butyric acid
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: 4-(4-Oxo-2-thioxo-thiazolidin-3-yl)-butyric acid
CAS number: 18623-60-4

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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: C7H9NO3S2
Molecular weight: 219.3

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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：

  4-(4-氧代-2-硫代氧基-3-噻唑基)丁酸 在 氯化亚砜 、 sodium acetate 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 反应 3.17h， 生成 4-[5-(1H-indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoyl chloride
  参考文献：
  名称：

  Synthesis and Primary Antitumor Screening of 4-[5-(1H-Indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamides

  摘要：

  A preparative procedure was developed for the synthesis of 4-[5-(1-R-1H-indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acids which were converted to acid chlorides, and the latter reacted with aromatic and heterocyclic amines to afford a series of previously unknown 4-[5-(1H-indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamides. The synthesized compounds showed a moderate antitumor activity against most malignant tumor cells. UO31 renal cancer cell line turned out to be most sensitive to most of the tested compounds.

  DOI：

  10.1134/s1070428020070040
• 作为产物：
  描述：

  4-Dithiocarboxyamino-butyric acid 在 盐酸 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 49.0h， 生成 4-(4-氧代-2-硫代氧基-3-噻唑基)丁酸
  参考文献：
  名称：

  5-(1H-Indol-3-ylmethylene)-4-oxo-2-thioxothiazolidin-3-yl) 链烷羧酸作为抗菌剂：合成、生物学评价和分子对接研究

  摘要：

  背景：传染病象征着全球对公共卫生安全造成的后果性压力，并对世界各地的社会经济稳定产生影响。对当前抗菌治疗的耐药性日益增加，迫切需要发现和开发具有不同作用模式的感染治疗新实体，这些实体可以同时针对敏感菌株和耐药菌株。方法：使用有机合成的经典方法合成化合物。结果：所有 20 种合成化合物均显示出对 8 种革兰氏阳性和革兰氏阴性细菌的抗菌活性。应该提到的是，所有化合物对所有测试的细菌都表现出比氨苄青霉素更好的抗菌效力。此外，18 种化合物似乎比链霉素更有效地对抗金黄色葡萄球菌、阴沟肠杆菌、铜绿假单胞菌、单核细胞增生李斯特菌和大肠杆菌。三种最活跃的化合物 4h、5b 和 5g 似乎比氨苄青霉素更有效地对抗 MRSA，而链霉素没有显示任何杀菌活性。与氨苄青霉素相比，所有三种化合物对铜绿假单胞菌和大肠杆菌的耐药菌株也显示出更好的活性。此外，所有化合物都能够比两种参考药物抑制生物膜形成多 2 到 4 倍

  DOI：

  10.3390/molecules25081964

文献信息

• Antibacterial properties of 5-substituted derivatives of rhodanine-3-carboxyalkyl acids
  作者：Waldemar Tejchman、Izabela Korona-Glowniak、Anna Malm、Marek Zylewski、Piotr Suder

  DOI：10.1007/s00044-017-1852-7

  日期：2017.6

  A series of rhodanine 3-carboxyalkanoic acid derivatives possessing 4′-(N,N-dialkyl-amino or diphenylamino)-benzylidene moiety as a substituent at the C-5 position were synthesised and their antibacterial activity was screened. All the rhodanine derivatives showed bacteriostatic or bactericidal activity to the reference gram-positive bacterial strains, but lack of activity to the reference Gram-negative

  合成了在C-5位具有4'-（N，N-二烷基氨基或二苯氨基）-亚苄基部分作为取代基的一系列若丹宁3-羧基链烷酸衍生物，并筛选了它们的抗菌活性。所有的罗丹宁衍生物均对参考革兰氏阳性细菌菌株具有抑菌或杀菌活性，但对参考革兰氏阴性细菌菌株和酵母菌株则缺乏活性。
• Discovery of 1,3-diphenyl-1H-pyrazole derivatives containing rhodanine-3-alkanoic acid groups as potential PTP1B inhibitors
  作者：Liangpeng Sun、Peipei Wang、Lili Xu、Lixin Gao、Jia Li、Huri Piao

  DOI：10.1016/j.bmcl.2019.03.023

  日期：2019.5

  Two series of 1,3-diphenyl-1H-pyrazole derivatives containing rhodanine-3-alkanoic acid groups were identified as competitive protein tyrosine phosphatase 1B (PTP1B) inhibitors. Among the compounds studied, IIIv was found to have the best in vitro inhibition activity against PTP1B (IC50 = 0.67 ± 0.09 µM) and the best selectivity (9-fold) between PTP1B and T-cell protein tyrosine phosphatase (TCPTP)

  含有若丹宁-3-链烷酸基团的两个系列的1,3-二苯基-1H-吡唑衍生物被确定为竞争性蛋白酪氨酸磷酸酶1B（PTP1B）抑制剂。在研究的化合物中，发现IIIv对PTP1B具有最佳的体外抑制活性（IC50 = 0.67±0.09 µM），并且在PTP1B和T细胞蛋白酪氨酸磷酸酶（TCPTP）之间具有最佳选择性（9倍）。分子对接研究表明，化合物IIIm，IIIv和IVg可同时在催化位点和相邻的PTyr结合位点占据。这些结果为设计PTP1B和其他PTP抑制剂提供了新的先导化合物。
• Spectral Characteristic and Preliminary Anticancer Activity <i>in vitro</i> of Selected Rhodanine-3-carboxylic Acids Derivatives
  作者：Iwona Stawoska、Waldemar Tejchman、Olga Mazuryk、Antonín Lyčka、Patrycja Nowak-Sliwinska、Ewa Żesławska、Wojciech Nitek、Agnieszka Kania

  DOI：10.1002/jhet.2897

  日期：2017.9

  Selected rhodanine‐3‐carboxylic acids derivatives were synthesized to determine the influence of the structure and the length of the linker between the carboxyl group and the nitrogen atom (N‐3) in the 2‐thioxo‐4‐thiazolidinone ring on their activity, monitored via interactions with human serum albumin. Based on fluorescence studies, we concluded that the length of the linker has a limited impact on

  合成了选定的若丹宁-3-羧酸衍生物，以确定2-硫代-4-噻唑烷酮环中羧基与氮原子（N-3）之间的连接结构和长度对其活性的影响，通过与人血清白蛋白的相互作用进行监测。基于荧光研究，我们得出的结论是，连接子的长度对这些相互作用的影响有限。此外，我们提出了对所有测试化合物进行淬灭的静态机理。这些衍生物似乎具有纳摩尔浓度范围的抗癌活性，其中3种是在A2780和A2780cisR细胞系中最有效的化合物。
• Synthesis of novel 1,3-diaryl pyrazole derivatives bearing rhodanine-3-fatty acid moieties as potential antibacterial agents
  作者：Li-Li Xu、Chang-Ji Zheng、Liang-Peng Sun、Jing Miao、Hu-Ri Piao

  DOI：10.1016/j.ejmech.2011.12.011

  日期：2012.2

  In the present study, a series of 1,3-diaryl pyrazole derivatives bearing rhodanine-3-fatty acid moieties were synthesized and their antimicrobial activities were tested against various Gram-positive and Gram-negative bacteria. 1,3-diaryl-4-formylpyrazoles were synthesized as key intermediates following a Vilsmeier–Haack strategy. Several compounds with an MIC of 2 μg/mL, exhibited stronger antibacterial

  在本研究中，合成了一系列带有若丹宁-3-脂肪酸部分的1,3-二芳基吡唑衍生物，并测试了它们对各种革兰氏阳性和革兰氏阴性细菌的抗菌活性。按照维尔斯迈尔-哈克（Vilsmeier-Haack）策略，合成了1,3-二芳基-4-甲酰基吡唑类化合物作为关键中间体。MIC为2μg/ mL的几种化合物显示出比对照更强的耐甲氧西林金黄色葡萄球菌（MRSA）的抗菌活性。这些化合物均未显示出对革兰氏阴性细菌的任何活性。
• The Crystal Structures of Three Rhodanine-3-Carboxylic Acids
  作者：Waldemar Tejchman、Agnieszka Skórska-Stania、Ewa Żesławska

  DOI：10.1007/s10870-016-0644-0

  日期：2016.4

  The rhodanine derivatives show various pharmacological activities. Rhodanine-3-carboxylic acids can be used as the substrates in various synthesis of compounds containing rhodanine-3-carboxyalkyl moiety. In this paper new crystal structures of rhodanine-3-acetic acid and its two homologues, i.e. rhodanine-3-propionic acid and rhodanine-3-butyric acid, are reported. The relationship between the length of the alkyl chain and the geometry of these molecules was studied. The crystal network is dominated by strong hydrogen bonds O–H···O formed by the carboxyl groups. Additionally, weak C–H···O and C–H···S contacts are observed. To study the difference in intermolecular interactions of rhodanine-3-carboxylic acid, three crystal structures were determined by X-ray diffraction method. The crystal network in all studied structures is built of homosynthons and stabilized by weak C–H···O and C–H···S contacts.

  罗丹宁衍生物显示出多种药理活性。罗丹宁-3-羧酸可以作为含有罗丹宁-3-羧烷基部分的各种化合物合成中的底物。本文报道了罗丹宁-3-乙酸及其两个同系物，即罗丹宁-3-丙酸和罗丹宁-3-丁酸的新晶体结构。研究了烷基链长度与这些分子几何形状之间的关系。晶体网络主要由羧基形成的强氢键O–H···O支配。此外，还观察到了弱的C–H···O和C–H···S接触。为了研究罗丹宁-3-羧酸分子间相互作用的差异，通过X射线衍射方法确定了三种晶体结构。所有研究结构中的晶体网络均由同源合成体构建，并通过弱的C–H···O和C–H···S接触稳定。