5-(2-噻吩基)-1,3,4-噻二唑-2-胺 | 4683-00-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-(2-噻吩基)-1,3,4-噻二唑-2-胺
• 中文别名: 5-(噻吩-2-基)-1,3,4-噻二唑-2-胺
• 英文名称: 5-(thiophen-2-yl)-1,3,4-thiadiazol-2-amine
• 英文别名: 2-amino-5-(2-thienyl)-1,3,4-thiadiazole；2-amino-5-thiophen-2-yl-1,3,4-thiadiazole；5-thiophen-2-yl-1,3,4-thiadiazol-2-amine
• CAS: 4683-00-5
• 化学式: C₆H₅N₃S₂
• mdl: MFCD01043763
• 分子量: 183.258
• InChiKey: DADKTCVAPDOGJQ-UHFFFAOYSA-N

物化性质

• 熔点：
  205-207 °C
• 沸点：
  379.8±34.0 °C(Predicted)
• 密度：
  1.497±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  108
• 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
• 危险类别：
  IRRITANT

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 2-Amino-5-(2-thienyl)-1,3,4-thiadiazole
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 2-Amino-5-(2-thienyl)-1,3,4-thiadiazole
CAS number: 4683-00-5

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C6H5N3S2
Molecular weight: 183.3

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

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

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-(2-噻吩基)-1,3,4-噻二唑-2-胺 在 乙酸哌啶酯 、 sodium carbonate 、 三氯氧磷 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 2.0h， 生成 5-{[6-(4-chlorophenyl)-2-thien-2-ylimidazo[2,1-b][1,3,4]thiadiazol-5-yl]methylene}-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis, Hypoglycaemic, Hypolipidemic and PPARγ Agonist Activities of 5-(2-Alkyl/aryl-6-Arylimidazo[2,1-b][1,3,4]thiadiazol-5-yl)methylene-1,3-Thiazolidinediones

  摘要：

  A novel series of 5‐(2‐alkyl/aryl‐6‐arylimidazo[2,1‐b][1,3,4]thiadiazol‐5‐yl)methylene‐1,3‐thiazolidinediones were synthesized as possible PPARγ agonists. The structures of these target molecules were established by spectral and analytical data. All the newly synthesized compounds were screened for their in vivo hypoglycaemic and hypolipidemic activity in male Wistar rats. Further, compounds with good activity were screened for PPARγ agonist activity. Among the screened compounds, 5‐{[2‐Cyclohexyl‐6‐(4‐methoxyphenyl)imidazo[2,1‐b] [1,3,4]thiadiazol‐5‐yl]methylene}‐1,3‐thiazolidine‐2,4‐dione (3i) exhibits promising hypoglycaemic and hypolipidemic activity via potential PPARγ agonist activity.

  DOI：

  10.1111/cbdd.12140
• 作为产物：
  描述：

  2-(2-噻吩亚甲基)肼-1-硫代甲酰胺 在 iron(III) chloride 作用下， 以 水 为溶剂， 生成 5-(2-噻吩基)-1,3,4-噻二唑-2-胺
  参考文献：
  名称：

  Cu(II) and Fe(III) Catalyzed Synthesis of Novel Thiophene Hybridized Thiadiazolyl Schiff Bases (TTS) as COX-2 Selective Inhibitor

  摘要：

  设计并合成了一系列新型噻吩杂化噻二唑基希夫碱 (TTS) 在硝酸铜（CuII）催化下合成希夫碱，随后在氯化铁（FeIII）催化下环化成噻二唑。 (FeIII) 催化环化成噻二唑。这些分子的设计灵感来自于 噻二唑、希夫碱和噻吩的抗炎特性。根据 质谱、红外光谱、1H 和 13C NMR 测量的信息，确定了最近合成的化合物的结构。 确定了最近合成的化合物的结构。进行分子对接的目的是为了更好地了解 候选药物与 COX-1（PDB ID：3KK6）和 COX-2（PDB ID：3Q7D）炎症相关靶点之间的相互作用。 炎症相关靶点之间的相互作用。化合物 3a-f 显示出与 COX-2 更稳定的结合复合物 (相比（-4.86 至 -5.94 kcal/mol），化合物 3a-f 与 COX-2 的结合复合物更为稳定（-8.09 至 -9.13 kcal/mol）。此外，在 在体内分析中，化合物 3a 与参考药物双氯芬酸相比，表现出卓越的抗炎活性。 有趣的是，利用 qRT-PCR 进行的 mRNA 表达分析表明，与 COX-2 相比，化合物 3a 对 COX-2 有特异性抑制作用。 与 COX-1 相比，COX-2 的 mRNA 表达得到了抑制，这进一步证实了之前的研究结果。总之，这些发现 为这些化合物作为新型先导分子开发提供了机会。 非甾体抗炎药的替代品。

  DOI：

  10.14233/ajchem.2023.27745

文献信息

• An investigation on photophysical and third–order nonlinear optical properties of novel thermally–stable thiophene–imidazo [2,1-b][1,3,4] thiadiazole based azomethines
  作者：Viprabha Kakekochi、Udaya Kumar D、Nikhil P. P、Keloth Chandrasekharan

  DOI：10.1016/j.dyepig.2019.04.033

  日期：2019.8

  further validated with the aid of theoretical calculations. Further, the azomethines TI1 and TI2 were subjected to Z–scan analysis to study the nonlinear optical (NLO) properties. The molecules exhibited effective two photon absorption (TPA) with the large nonlinear absorption coefficient (βeff) of the order of 10−10 m W−1. The planar structure of TI1 furnished a better interaction between donor and

  由于容易进行结构修改和解决方案的可加工性，导致柔性的大面积光电器件中π共轭半导体材料的使用在全世界范围内得到了广泛应用，从而导致了光电特性的变化。在这种情况下，设计并合成了新型的噻吩和咪唑并[2,1- b ] [1,3,4]噻二唑（ITD）共轭偶氮甲胺（TI1-TI3）。实验研究了合成的偶氮甲碱（TI1-TI3）的光物理和电化学性质，并在理论计算的基础上进一步进行了验证。此外，偶氮甲碱TI1和TI2进行了Z扫描分析，以研究非线性光学（NLO）特性。该分子与大的非线性的吸收系数（表现出有效的双光子吸收（TPA）β EFF的10级）-10 男女-1。的平面结构TI1提供供体和受体部分之间的更好的相互作用和扩展的π共轭，提供一种改进的β EFF（0.81×10 -10 米w ^ -1）至TI1相比的TI2（0.55×10 -10  m W -1）。从结果推断，分子可能是有效光子器件中使用的潜在材料。
• N-thiadiazole-4-hydroxy-2-quinolone-3-carboxamides bearing heteroaromatic rings as novel antibacterial agents: Design, synthesis, biological evaluation and target identification
  作者：Wenjie Xue、Xueyao Li、Guixing Ma、Hongmin Zhang、Ya Chen、Johannes Kirchmair、Jie Xia、Song Wu

  DOI：10.1016/j.ejmech.2019.112022

  日期：2020.2

  new class of antibacterial agents, as one of its derivatives was identified as an antibacterial agent against S. aureus. However, no potency-directed structural optimization has been performed. In this study, we designed and synthesized 37 derivatives, and evaluated their antibacterial activity against S. aureus ATCC29213, which led to the identification of ten potent antibacterial agents with minimum

  由于发生抗生素抗性，细菌感染性疾病已成为对公共健康的严重威胁。为了克服抗生素抗性，迫切需要新型抗生素。N-噻二唑-4-羟基-2-喹诺酮-3-羧酰胺是一类潜在的新型抗菌剂，因为其衍生物之一被确定为针对金黄色葡萄球菌的抗菌剂。但是，尚未执行效能导向的结构优化。在这项研究中，我们设计和合成了37种衍生物，并评估了它们对金黄色葡萄球菌ATCC29213的抗菌活性，从而鉴定出十种有效抑菌剂，其最低抑菌浓度（MIC）值均低于1μg/ mL。接下来，我们针对一组抗药性临床分离株进行了细菌生长抑制测定，包括耐甲氧西林的金黄色葡萄球菌，以及对HepG2和HUVEC细胞的细胞毒性测定。一种被测试的化合物，称为1-乙基-4-羟基-2-氧代-N-（5-（噻唑-2-基）-1,3,4-噻二唑-2-基）-1,2-二氢喹啉-与万古霉素相比，3-羧酰胺（g37）对被测菌株的抗菌力（MIC：0.25-1μg/ mL对1-64μg/
• Antihypertensive thiadiazoles. 1. Synthesis of some 2-aryl-5-hydrazino-1,3,4-thiadiazoles with vasodilator activity
  作者：Stephen Turner、Malcolm Myers、Brian Gadie、Anthony J. Nelson、Robin Pape、John F. Saville、John C. Doxey、Timothy L. Berridge

  DOI：10.1021/jm00400a003

  日期：1988.5

  with a 2-substituted phenyl ring had higher activity than their 3- or 4-substituted counterparts or those containing heteroaryl groups. The 2-methylphenyl and 2-ethylphenyl derivatives 7 and 18 were the most potent members of the series. Preliminary studies indicated that the hypotensive action of these compounds was due to a direct relaxant effect on vascular smooth muscle.

  已经合成了一些2-芳基-5-肼基-1,3,4-噻二唑并筛选了其降压活性。通常，具有2-取代的苯环的化合物比其3-或4-取代的对应物或含有杂芳基的化合物具有更高的活性。2-甲基苯基和2-乙基苯基衍生物7和18是该系列中最有效的成员。初步研究表明，这些化合物的降压作用归因于对血管平滑肌的直接松弛作用。
• Synthesis and Antifungal Activities of Drimane-Amide Derivatives from Sclareol
  作者：Miaofeng Ma、Jili Feng、Dezhi Wang、Shu-Wei Chen、Hui Xu

  DOI：10.2174/1386207321666180925164358

  日期：2018.11.15

  displayed higher fungicidal activity than sclareol against all the tested phytopathogenic fungi, and were more effective than the positive control thiabendazole against A. alternate and A. brassicae. The structure-activity relationship studies of compounds A1-10 indicated that both the position and type of substituent on the phenyl ring had significant effects on antifungal activity. CONCLUSION The

  目的和目标植物病害是由真菌病原体引起的，导致许多农作物遭受严重的经济损失。而且，许多真菌对常用抗真菌剂的抵抗力不断增强，因此有必要发现和开发新的杀菌剂。因此，本研究的重点是合成新型骨架化合物以有效控制植物病害。材料与方法设计了一系列的十二烷酰胺衍生物，是通过胺与香紫苏醇制备的中间体香紫苏内酯的氨解反应合成的。使用1H NMR，13C NMR和HRMS（ESI）光谱数据确认了所有合成化合物的结构。通过使用菌丝体生长速率方法初步评估了它们的体外抗真菌活性，该方法对五种植物病原真菌：灰葡萄孢菌，格氏小球藻，交替链格孢，铜链格孢和禾谷镰刀菌。结果成功获得23种目标化合物，收率52-95％。化合物A2和A3对B. cinerea，G。cingulata和A. brasicae表现出良好的抑制作用，IC50值在3.18至10.48 µg / mL之间。这两种化合物对所有测试的植物病原真菌均具有比香紫苏
• 具有2-氨基-1,3,4-噻二唑结构的α-氨基膦酸酯化合物及其制备方法与用途
  申请人：广西师范学院

  公开号：CN106117268A

  公开（公告）日：2016-11-16

  本发明公开了一种具有2‑氨基‑1,3,4‑噻二唑结构的α‑氨基膦酸酯化合物及其制备方法与用途，本发明所述的具有2‑氨基‑1,3,4‑噻二唑结构的α‑氨基膦酸酯化合物具有α‑氨基膦酸酯化合物杀菌的通性，同时引入2‑氨基‑1,3,4‑噻二唑基团的杀虫性能，两者结合使得化合物的用途更加广泛，杀菌和杀虫效果更加好。本发明所述的制备方法步骤少，操作简单，但是产量和产率高，在实际生产中能够节省大量的时间和成本，经济效益好。本发明的2‑氨基‑1,3,4‑噻二唑对番茄早疫菌的生长增殖具有抑制作用，对粘虫具有抑制生长作用，可作为农药中间体应用于不同农用杀菌剂的制造和用途。