5-(4-iodophenyl)-1,3,4-thiadiazol-2-amine | 70057-74-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(4-iodophenyl)-1,3,4-thiadiazol-2-amine
• CAS: 70057-74-8
• 化学式: C₈H₆IN₃S
• 分子量: 303.126
• InChiKey: HHIOSVWTRQDIFU-UHFFFAOYSA-N

物化性质

• 熔点：
  92-93 °C(Solvent: Ethanol ; Water)
• 沸点：
  416.6±47.0 °C(Predicted)
• 密度：
  1.955±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 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：
  80
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-iodophenyl)-1,3,4-thiadiazol-2-amine 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成
  参考文献：
  名称：

  Novel imidazo[2,1-b]-1,3,4-thiadiazoles as promising antifungal agents against clinical isolate of Cryptococcus neoformans

  摘要：

  We herein report the synthesis and in vitro antimicrobial evaluation of twenty five novel hybrid derivatives of imidazo [2,1-b]-1,3,4-thiadiazole containing chalcones (5a-o) and Schiff bases (6a-j) against three fungal strains (Candida albicans, Cryptococcus neoformans and Asperg-illus niger). Most of the tested compounds displayed substantial anti-fungal activity with MICs ranging between 1.56 and 100 mu g/mL. Compounds 5a, 5b and 5n exhibited promising activity against C neoformans at a MIC 1.56 mu g/mL. In addition, compound 5n also demonstrated significant antifungal activity against the clinical isolates of C neoformans at MIC 3.125 mu g/mL. However, moderate activity was observed for these compounds against four bacterial strains (Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa) and Mycobacterium tuberculosis (H(37)Rv). (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.03.021
• 作为产物：
  描述：

  4-碘苯甲酸 、 氨基硫脲 在 三氯氧磷 作用下， 反应 3.0h， 以70%的产率得到5-(4-iodophenyl)-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  一系列 1,3,4-硫属元素二唑的晶体结构中氢键、卤素键和硫属元素键之间的平衡

  摘要：

  为了探索特定的原子间置换如何改变 1,3,4-硫属元素二唑衍生物的静电势，并有意改变分子间相互作用之间的平衡，合成并表征了四个目标分子。DFT 计算表明，与分子间氢键相比，Br 与 I 的原子间取代和 S 与 Se 的原子间取代增强了 σ 空穴势，从而提高了卤素键和硫属元素键的结构导向能力。5-(4-碘苯基)-1,3,4-噻二唑-2-胺的两种多晶型物的形成进一步强调了这些分子间作用力之间的微妙平衡；I型显示所有三种相互作用，而II型仅显示氢和硫属元素键合。

  DOI：

  10.3390/molecules26144125

文献信息

• Multicomponent reaction for the synthesis of new 1,3,4-thiadiazole-thiazolidine-4-one molecular hybrids as promising antidiabetic agents through α-glucosidase and α-amylase inhibition
  作者：Lalitha Gummidi、Nagaraju Kerru、Oluwakemi Ebenezer、Paul Awolade、Olakunle Sanni、Md. Shahidul Islam、Parvesh Singh

  DOI：10.1016/j.bioorg.2021.105210

  日期：2021.10

  simple and efficient protocol was developed to synthesize a new library of thiazolidine-4-one molecular hybrids (4a-n) via a one-pot multicomponent reaction involving 5-substituted phenyl-1,3,4-thiadiazol-2-amines, substituted benzaldehydes and 2-mercaptoacetic acid. The synthesized compounds were evaluated in vitro for their antidiabetic activities through α-glucosidase and α-amylase inhibition as well

  开发了一种简单有效的方案，通过涉及 5-取代苯基-1,3,4-噻二唑-2-胺的一锅多组分反应合成新的噻唑烷-4-one 分子杂化物 ( 4a-n )库，取代的苯甲醛和 2-巯基乙酸。通过抑制α-葡萄糖苷酶和α-淀粉酶以及它们的抗氧化和抗菌潜力，体外评估合成的化合物的抗糖尿病活性。化合物4e表现出最有希望的α-葡萄糖苷酶和α-淀粉酶抑制作用，IC 50值为 2.59 μM，与标准抑制剂阿卡波糖相比，分别高出约 1.5 倍和 14 倍。构效关系（SAR）分析表明，苯环上取代基的性质和位置对抑制效力有显着影响。
• Improved antiproliferative activity of 1,3,4-thiadiazole-containing histone deacetylase (HDAC) inhibitors by introduction of the heteroaromatic surface recognition motif
  作者：Peng Guan、Lei Wang、Xuben Hou、Yichao Wan、Wenfang Xu、Weiping Tang、Hao Fang

  DOI：10.1016/j.bmc.2014.09.039

  日期：2014.11

  A series of 1,3,4-thiadiazole-containing hydroxamic acids, in accord with the common pharmacophore of histone deacetylase (HDAC) inhibitors (a Zn2+ binding moiety-a linker-a surface recognition motif), was identified as submicromolar HDAC inhibitors by our group. In this study, we continued our efforts to develop 1,3,4-thiadiazole bearing hydroxamate analogues by modifying the surface recognition motif. We found that 1,3,4-thiadiazoles having a heteroaromatic substituent showed better HDAC inhibitory activity in enzymatic assay and higher antiproliferative potency in cellular assay compared to SAHA. (C) 2014 Elsevier Ltd. All rights reserved.
• Salih, Nadia; Salimon, Jumat; Yousif, Emad, Oriental Journal of Chemistry, 2011, vol. 27, # 2, p. 373 - 383
  作者：Salih, Nadia、Salimon, Jumat、Yousif, Emad

  DOI：——

  日期：——
• Salimon, Jumat; Salih, Nadia; Ibraheem, Hanan, Asian Journal of Chemistry, 2010, vol. 22, # 7, p. 5289 - 5296
  作者：Salimon, Jumat、Salih, Nadia、Ibraheem, Hanan、Yousif, Emad

  DOI：——

  日期：——
• Novel imidazo[2,1-b]-1,3,4-thiadiazoles as promising antifungal agents against clinical isolate of Cryptococcus neoformans
  作者：Wesam S. Alwan、Rajshekhar Karpoormath、Mahesh B. Palkar、Harun M. Patel、Rajesh A. Rane、Mahamadhanif S. Shaikh、Afsana Kajee、Koleka P. Mlisana

  DOI：10.1016/j.ejmech.2015.03.021

  日期：2015.5

  We herein report the synthesis and in vitro antimicrobial evaluation of twenty five novel hybrid derivatives of imidazo [2,1-b]-1,3,4-thiadiazole containing chalcones (5a-o) and Schiff bases (6a-j) against three fungal strains (Candida albicans, Cryptococcus neoformans and Asperg-illus niger). Most of the tested compounds displayed substantial anti-fungal activity with MICs ranging between 1.56 and 100 mu g/mL. Compounds 5a, 5b and 5n exhibited promising activity against C neoformans at a MIC 1.56 mu g/mL. In addition, compound 5n also demonstrated significant antifungal activity against the clinical isolates of C neoformans at MIC 3.125 mu g/mL. However, moderate activity was observed for these compounds against four bacterial strains (Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa) and Mycobacterium tuberculosis (H(37)Rv). (C) 2015 Elsevier Masson SAS. All rights reserved.