5-(异丙基硫基)-1,3,4-噻二唑-2-胺 | 30062-47-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 5-(异丙基硫基)-1,3,4-噻二唑-2-胺
• 英文名称: 5-(isopropylthio)-1,3,4-thiadiazol-2-amine
• 英文别名: 5-(Isopropylsulfanyl)-1,3,4-thiadiazol-2-amine；5-propan-2-ylsulfanyl-1,3,4-thiadiazol-2-amine
• CAS: 30062-47-6
• 化学式: C₅H₉N₃S₂
• mdl: MFCD00925753
• 分子量: 175.279
• InChiKey: QCMMKDSALYWVRF-UHFFFAOYSA-N

物化性质

• 熔点：
  147-150 °C
• 沸点：
  320.8±25.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-(Isopropylsulfanyl)-1,3,4-thiadiazol-2-amine
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: 5-(Isopropylsulfanyl)-1,3,4-thiadiazol-2-amine
CAS number: 30062-47-6

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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, refrigerated.
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: C5H9N3S2
Molecular weight: 175.3

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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：

  5-(异丙基硫基)-1,3,4-噻二唑-2-胺 在 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 2-(N-methyl)-acetylamino-5-iso-propyl-mercapto-1,3,4-thiadiazole
  参考文献：
  名称：

  Synthesis of 2-Amino-5-sulfanyl-1,3,4-thiadiazole Derivatives and Evaluation of Their Antidepressant and Anxiolytic Activity

  摘要：

  Recently a series of 2-amino-5-sulfanyl-1,3,4-thiadiazole derivatives bearing different substituents were synthesized and screened pharmacologically in order to evaluate their central nervous system activity. The purpose of this study was to evaluate the effects of the title compounds on CNS activity by varying the substituents in the thiadiazole moiety. It was found that some of these compounds possess marked antidepressant and anxiolytic properties comparable in efficiency to the reference drugs Imipramine and Diazepam. The most potent compound 3k was further investigated to complete its pharmacological profile with respect to undesired side effects. Behavioral results showed that 3k is a very promising compound, characterized by a mixed antidepressant-anxiolytic activity accompanied by a therapeutic dose range that is essentially 2 orders of magnitude less than that at which side effects such as sedation and amnesia are evident.

  DOI：

  10.1021/jm001027w
• 作为产物：
  描述：

  sodium 2-amino-5-mercapto-1,3,4-thiadiazolate 生成 5-(异丙基硫基)-1,3,4-噻二唑-2-胺
  参考文献：
  名称：

  SUIKO M.; MAEKAWA K., AGR. AND BIOL. CHEM. , 1977, 41, NO 10, 2047-2053

  摘要：

  DOI：

文献信息

• Synthesis and in vitro Evaluation of West Nile Virus Protease Inhibitors Based on the 1,3,4,5‐Tetrasubstituted 1 <i>H</i> ‐Pyrrol‐2(5 <i>H</i> )‐one Scaffold
  作者：Yaojun Gao、Sanjay Samanta、Taian Cui、Yulin Lam

  DOI：10.1002/cmdc.201300244

  日期：2013.9

  1H‐pyrrol‐2(5H)‐one scaffold was identified by screening a small library of nonpeptidic compounds. Optimization of this initial hit by the synthesis and screening of a focused library of compounds with this scaffold led to the identification of a novel uncompetitive inhibitor ((−)‐1a16, IC50=2.2±0.7 μM) of the WNV NS2B–NS3 protease. Molecular docking of the chiral compound onto the WNV protease indicates

  西尼罗河病毒（WNV）是黄病毒科的成员，是一种由蚊子传播的病原体，每年引起大量人类感染。目前尚无可用于人类的针对WNV的疫苗或抗病毒疗法。因此，迫切需要开发针对该病毒的新化学疗法。在这项研究中，通过筛选一个小的非肽类化合物文库，鉴定了具有1,3,4,5-四取代的1 H-吡咯-2（5 H）-one支架的WNV NS2B–NS3蛋白酶抑制剂。该初始命中通过合成的优化和化合物与本支架导致的新颖非竞争性抑制剂的鉴定（（聚焦文库的筛选- ） - 1a16，IC 50 = 2.2±0.7μ中号）的WNV NS2B– 蛋白酶。手性化合物与WNV蛋白酶的分子对接表明1a16的R 对映体干扰了NS2B辅因子和 蛋白酶结构域之间的生产性相互作用，因此是抑制WNV NS2B– 蛋白酶的优选异构体。
• Design, Synthesis, Antibacterial Activity, and Mechanisms of Novel 1,3,4-Thiadiazole Derivatives Containing an Amide Moiety
  作者：Zhibing Wu、Jin Shi、Jixiang Chen、Deyu Hu、Baoan Song

  DOI：10.1021/acs.jafc.1c01626

  日期：2021.8.11

  To discover novel antibacterial agents, a series of novel 1,3,4-thiadiazole derivatives containing an amide moiety were designed and synthesized, and their antibacterial activities were tested. Compound 30 was designed and synthesized according to the CoMFA model. Compound 30 exhibited higher antibacterial activities against Xanthomonas oryzae pv. oryzicola and Xanthomonas oryzae pv. oryzae, with EC50

  为了发现新型抗菌剂，设计并合成了一系列含有酰胺部分的新型 1,3,4-噻二唑衍生物，并测试了它们的抗菌活性。化合物30是根据CoMFA模型设计合成的。化合物30对米黄单胞菌有较高的抗菌活性。oryzicola和Xanthomonas oryzae pv。oryzae 的EC 50值分别为 2.1 和 1.8 mg/L，优于硫代二唑铜（99.6 和 92.5 mg/L）。化合物30的保护和治疗活性对水稻白叶枯病的抑制率分别为 51.3% 和 46.1%，优于硫代二唑铜（37.8% 和 38.5%）。化合物30对水稻细菌性条斑病的保护和治疗活性分别为45.9%和40.5%，优于硫代二唑铜（36.2%和31.1%）。此外，化合物30对水稻细菌性叶斑病的保护活性与相关防御酶的活性增加有关，并上调糖酵解/糖异生途径的差异表达蛋白。
• Synthesis and Evaluation of 1,3,4‐Thiadiazole Derivatives Containing Cyclopentylpropionamide as Potential Antibacterial Agent
  作者：Min Zhang、Weiming Xu、Kun Wei、Hongwu Liu、Qin Yang、Qin Liu、Liyun Yang、Yuqin Luo、Wei Xue

  DOI：10.1002/jhet.3576

  日期：2019.7

  to identify new strategies for the control of these plant bacterial diseases by combining a pharmacophoric group of different bioactive compounds. A series of 3‐cyclopentylpropionamide containing 1,3,4‐thiadiazole derivatives was synthesized and characterized via 1H‐NMR, 13C‐NMR, and HRMS. Bioassay results indicated that compounds 7a, 7d, 7j, 7m, 7n, and 7s had excellent antibacterial activity compared

  这项研究旨在通过组合不同生物活性化合物的药效基团来确定控制这些植物细菌疾病的新策略。合成了一系列包含1,3,4-噻二唑衍生物的3-环戊基丙酰胺，并通过 1 H-NMR，13 C-NMR和HRMS进行了表征。生物测定结果表明，与阳性对照相比，化合物7a，7d，7j，7m，7n和7s具有优异的抗菌活性。其中，化合物7a以EC 50表现出对Xoo的显着抑制作用。含量为21.41μg/ mL，超过了噻二唑铜（67.71μg/ mL）和比美噻唑（69.05μg/ mL）。温室条件测试进一步显示图7a具有大约等于治疗活性和更好的保护活性（41.58％）抗水稻比噻铜和叶枯唑（分别为46.86和42.25％）的细菌性叶枯病。结构-活性关系分析表明，砜片段有利于抑制。总体而言，这项研究表明，含有1,3,4-噻二唑3-环戊基丙酰胺的衍生物可以用作杀菌剂研究的新的先导化合物。
• Antilipidemic Agents, III: Synthesis of Some Heterocyclic Derivatives of β-Sitosterol
  作者：N. S. Habib、M. A. Khalil

  DOI：10.1002/ardp.19903230705

  日期：——

  Four novel series of heterocyclic derivatives of β‐sitosterol were prepared by the reaction of 3‐β‐sitosterol hemisuccinate with SOCl2 then with thiols, amines or phenols. These series are: 3β‐[(3‐substituted‐4(3H)‐quinazolinon‐2‐yl)thiocarbonylproprionyloxy]stigmast‐5‐ene; 3β([4‐substituted‐5‐(4‐pyridyl)‐4H‐1,2,4‐triazol‐3‐yl]thiocarbonylpropionyloxy}stigmast‐5‐ene; 3β‐[(5‐substituted‐1,3,4‐thiad

  通过3-β-谷甾醇半琥珀酸酯与SOCl2反应，然后与硫醇、胺或酚反应，制备了四个新型β-谷甾醇杂环衍生物。这些系列是：3β-[(3-取代-4(3H)-喹唑啉酮-2-基)硫代羰基丙酰氧基]柱头-5-烯；3β([4-取代-5-(4-吡啶基)-4H-1,2,4-三唑-3-基]硫代羰基丙酰氧基}柱头-5-烯；3β-[(5-取代-1,3,4 -噻二唑-2-基)氨基甲酰基丙酰氧基] stigmast-5-烯和3β-取代的氨基甲酰基或氧羰基丙酰氧基) stigmast-5-烯。研究了代表性化合物的抗血脂活性。
• Synthesis and antimicrobial activity of N-[5-(4-t-amino-2-butynyl)thio-1,3,4-thiadiazol-2-yl]-2-carbamates
  作者：ME Zuhair、A Abu-Al-Teman、FA Hussein、SR Salman、D Al-Dujaili、VF Roche

  DOI：10.1016/0223-5234(92)90096-j

  日期：1992.3

  Three series of 5-thio-1,3,4-thiadiazole carbamates containing alkynyl, aminoalkynyl, alkenyl or alkyl thio substituents have been synthesized as potential antimicrobial agents. The influence of both the alkynyl linkage and the various terminal nitrogen heterocyclic moieties on antimicrobial activity was assessed utilizing representative Gram-positive, Gram-negative and fungal species. Mannich base analogs containing a 2-ethyl carbamate group and a nitrogen heterocyclic of limited bulk provided the broadest spectrum of antimicrobial activity. The thiadiazole carbamates containing a 5-alkylthio substituent were consistently active against the Pseudomonas and Candida organisms studied. It is concluded that an acetylenic linkage is not an absolute requirement for potent antimicrobial activity in this molecular series, and that the binding sites of the organisms tested exhibit a steric requirement for lipophilic, but non-bulky, amine-containing heterocycles on Mannich base analogs.