2-amino-5-(5-nitro-2-thienyl)-1,3,4-thiadiazole | 499993-55-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-amino-5-(5-nitro-2-thienyl)-1,3,4-thiadiazole
• 英文别名: 5-(5-Nitrothiophen-2-yl)-1,3,4-thiadiazol-2-amine
• CAS: 499993-55-4
• 化学式: C₆H₄N₄O₂S₂
• 分子量: 228.255
• InChiKey: VSGOBUZDOQMNJP-UHFFFAOYSA-N

物化性质

• 熔点：
  210-211 °C(Solv: ethanol (64-17-5))
• 沸点：
  469.5±55.0 °C(Predicted)
• 密度：
  1.700±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 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：
  154
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-amino-5-(5-nitro-2-thienyl)-1,3,4-thiadiazole 在 盐酸 、 铜 、 硫脲 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 生成 2-mercapto-5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazole
  参考文献：
  名称：

  某些[5-（硝基芳基）-1,3,4-噻二唑-2-基硫代]丙酸烷基酯的合成及抗分枝杆菌活性。

  摘要：

  合成了两个系列的2-和3- [5-（硝基芳基）-1,3,4-噻二唑-2-基硫代，亚磺酰基和磺酰基]丙酸烷基酯，并使用BACTEC 460筛选了针对结核分枝杆菌H37Rv的抗结核活性辐射测量系统。确定显示超过90％抑制作用的化合物的MIC值。两组数据的比较结果表明，在合成的衍生物中，化合物丙基3- [5-（5-硝基噻吩-2-基）-1,3,4-噻二唑-2-基硫代]丙酸酯最大。活性化合物（MIC = 1.56 microgml（-1））。

  DOI：

  10.1016/j.bmcl.2005.11.087
• 作为产物：
  描述：

  2-((5-nitrothiophen-2-yl)methylene)hydrazinecarbothioamide 在 ammonium iron(III) sulfate 作用下， 以 水 为溶剂， 生成 2-amino-5-(5-nitro-2-thienyl)-1,3,4-thiadiazole
  参考文献：
  名称：

  具有某些含硫烷基侧链的5-（硝基芳基）-1,3,4-噻二唑的合成及抗幽门螺杆菌活性。

  摘要：

  合成了一系列5-（硝基芳基）-1,3,4-噻二唑，它们带有类似于替硝唑分子中侧基的某些含硫烷基侧链，并使用圆盘扩散法对幽门螺杆菌进行了评估。还评估了合成的化合物的抗菌，抗真菌和细胞毒性作用。对这一系列化合物的构效关系的研究表明，硝基芳基单元的结构和1,3,4-噻二唑环2位上的侧基均显着影响抗H。幽门螺杆菌活动。尽管含有硝基噻吩系列中2- [2-（乙基磺酰基）乙硫基]侧链的化合物7a是针对幽门螺杆菌临床分离株测试的最有效的化合物，硝基咪唑6c和7c由于具有抗H的特性而被认为是更有前途的化合物。幽门螺杆菌活性除细胞毒性作用较小外。

  DOI：

  10.1016/j.bmcl.2008.04.033

文献信息

• Synthesis and Biological Activity of Nitro Heterocycles Analogous to Megazol, a Trypanocidal Lead
  作者：Gérard Chauvière、Bernard Bouteille、Bertin Enanga、Cristina de Albuquerque、Simon L. Croft、Michel Dumas、Jacques Périé

  DOI：10.1021/jm021030a

  日期：2003.1.1

  the two rings of the basic nucleus, replacement of the thiadiazole by an oxadiazole, replacement of the nitroimidazole part by a nitrofurane or a nitrothiophene, and substitutions on the exocyclic nitrogen atom for evaluation of an improved import by the glucose or the purine transporters. Assays of the series of compounds on the protozoan parasites Trypanosoma brucei, Trypanosoma cruzi, and Leishmania

  作为我们开发旨在治疗寄生虫感染的新化合物的努力的一部分，我们合成并测定了主要化合物megazol 5-（1-甲基-5-硝基-1H-2-咪唑基）-1,3的类似物， 4-噻二唑-2-胺，CAS号 19622-55-0），体外。我们首先开发了一条合成巨z的新途径。随后引入了一些结构变化，包括在碱性原子核的两个环上进行取代，用二恶唑取代噻二唑，用硝基呋喃或硝基噻吩取代硝基咪唑部分以及在环外氮原子上进行取代，以评估其改进之处。由葡萄糖或嘌呤转运蛋白进口。对原生动物寄生虫布鲁氏锥虫，克鲁斯锥虫和多形利什曼原虫的一系列化合物的分析，不论是细胞外细胞还是被感染的巨噬细胞，都表明兆唑比衍生物更具活性。然后，对感染了布氏锥虫锥虫的灵长类动物（包括晚期中枢神经系统感染和苏拉明）进行了Megazol评估。在研究中，五只猴子观察到完全恢复，在两年的随访中没有寄生虫病复发。由于缺乏有效的治疗非洲昏睡病和南美南美锥虫病
• Design and development of ((4-methoxyphenyl)carbamoyl) (5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazol-2-yl)amide analogues as Mycobacterium tuberculosis ketol-acid reductoisomerase inhibitors
  作者：Vagolu Siva Krishna、Shan Zheng、Estharla Madhu Rekha、Radhika Nallangi、D.V. Sai Prasad、Shilpa E. George、Luke W. Guddat、Dharmarajan Sriram

  DOI：10.1016/j.ejmech.2020.112178

  日期：2020.5

  Based on our previous finding that the titled compound possesses anti-tuberculosis activity, a series of novel ((4-methoxyphenyl)carbamoyl) (5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazol-2-yl)amide analogues have been synthesized. Amongst the 22 compounds synthesized and tested, 5b, 5c and 6c showed potent inhibitory activity with K-i values of 2.02, 5.48 and 4.72 mu M for their target, Mycobacterium tuberculosis (Mt) ketol-acid reductoisomerase (KARI). In addition, these compounds have excellent in vitro activity against Mt H37Rv with MIC values as low as 1 mu M. The mode of binding for these compounds to Mt KARI was investigated through molecular docking and dynamics simulations. Furthermore, these compounds were evaluated for their activity in Mt infected macrophages, and showed inhibitory activities with up to a 1.9-fold reduction in growth (at 10 mM concentration). They also inhibited Mt growth in a nutrient starved model by up to 2.5-fold. In addition, these compounds exhibited low toxicity against HEK 293T cell lines. Thus, these compounds are promising Mt KARI inhibitors that can be further optimized into anti-tuberculosis agents. (c) 2020 Elsevier Masson SAS. All rights reserved.
• Discovery of a novel nitroimidazolyl–oxazolidinone hybrid with potent anti Gram-positive activity: Synthesis and antibacterial evaluation
  作者：Ali Khalaj、Maryam Nakhjiri、Amir Soheil Negahbani、Marjaneh Samadizadeh、Loghman Firoozpour、Saeed Rajabalian、Nasrin Samadi、Mohammad Ali Faramarzi、Neda Adibpour、Abbas Shafiee、Alireza Foroumadi

  DOI：10.1016/j.ejmech.2010.10.015

  日期：2011.1

  A number of linezolid analogues containing a nitroaryl-1,3,4-thiadiazole moiety, were prepared and evaluated as antibacterial agents against a panel of Gram-positive and Gram-negative bacteria. Among synthesized compounds, nitrofuran analogue 1b exhibited more potent inhibitory activity, with respect to other synthesized compounds and reference drug linezolid. The target compounds were also assessed for their cytotoxic activity against normal mouse fibroblast (NIH/3T3) cells using MTT assay. The results indicated that compound 1c exhibit potent antibacterial activity against Gram-positive bacteria at non-cytotoxic concentrations. (C) 2010 Elsevier Masson SAS. All rights reserved.
• New 5-(nitroheteroaryl)-1,3,4-thiadiazols containing acyclic amines at C-2: synthesis and SAR study for their antileishmanial activity
  作者：Azar Tahghighi、Saeed Emami、Sepide Razmi、Farzane Rezazade Marznaki、Sussan Kabudanian Ardestani、Siavoush Dastmalchi、Farzad Kobarfard、Abbas Shafiee、Alireza Foroumadi

  DOI：10.3109/14756366.2012.689297

  日期：2013.8.1

  A novel series of 5-(5-nitrofuran-2-yl)-and 5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazole-2-amines bearing acyclic amine at C-2 position of thiadiazole ring were synthesized and evaluated in vitro against promastigote and amastigote forms of Leishmania major. The structure-activity of series was investigated by studying 40 compounds. The most active derivatives were hydroxypropylamino-and methoxypropylamino-analogs of 5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazole (compounds 29 and 32, respectively) with highest selectivity index (SI > 12).
• Synthesis and in vitro anti-leishmanial activity of 1-[5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl]- and 1-[5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazol-2-yl]-4-aroylpiperazines
  作者：Mina Behrouzi-Fardmoghadam、Fatemeh Poorrajab、Sussan Kaboudanian Ardestani、Saeed Emami、Abbas Shafiee、Alireza Foroumadi

  DOI：10.1016/j.bmc.2008.02.052

  日期：2008.4

  The synthesis and anti-leishmanial activity of nitroheteroaryl-1,3,4-thiadiazole- based compounds including 1-[5-(5-nitrofuran2- yl)-1,3,4-thiadiazol-2-yl]-4-aroylpiperazines and 1-[5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazol-2-yl]-4-aroylpiperazines were described. Most of the synthesized compounds exhibited potent anti-leishmanial activity against both promastigote and amastigote forms of Leishmania major at non-cytotoxic concentrations. In general, 5- nitrofuran derivatives were more active than the corresponding 5- nitrothiophene analogues. (c) 2008 Elsevier Ltd. All rights reserved.