5-(3,4-二甲氧基-苯基)-[1,3,4]噻二唑-2-胺 | 5427-87-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-(3,4-二甲氧基-苯基)-[1,3,4]噻二唑-2-胺
• 英文名称: 5-(3,4-dimethoxyphenyl)-1,3,4-thiadiazol-2-amine
• CAS: 5427-87-2
• 化学式: C₁₀H₁₁N₃O₂S
• mdl: MFCD00981427
• 分子量: 237.282
• InChiKey: BQOCMHOWHOMIMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  98.5
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

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

反应信息

• 作为反应物：
  描述：

  5-(3,4-二甲氧基-苯基)-[1,3,4]噻二唑-2-胺 在 tin(II) chloride dihdyrate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 2-bromo-N-{3-[2-(3,4-dimethoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl]phenyl}acrylamide
  参考文献：
  名称：

  Design, synthesis and antiproliferative activity of novel heterobivalent hybrids based on imidazo[2,1- b ][1,3,4]thiadiazole and imidazo[2,1- b ][1,3]thiazole scaffolds

  摘要：

  Heterobivalent ligands constituted by two different pharmacophores that bind to different molecular targets or to two distinct sites on the same molecular target could be one of the methods used for the treatment of cancer. In view of the importance of imidazo[1,2-6][1,3]thiazole and imidazo[1,2-b][1,3,4] thiadiazole as privileged structures for the preparation of novel anticancer agents, we decided to explore the synthesis and biological evaluation of molecular conjugates comprising these fused bicyclic systems tethered at their C-6 position by a meta-(alpha-bromoacryloylamido)phenyl moiety. We found that most of the hybrid compounds displayed high antiproliferative activity toward a wide panel of cancer cell lines, with one-digit micromolar to submicromolar 50% inhibitory concentrations (IC50). We have observed that selected compounds 7d, 7e, 7n and 8c induced apoptosis, which was associated with the release of cytochrome c and cleavage of multiple caspases. Overexpression of the protective mitochondrial protein Bcl-2 did not confer protection to cell death induced by these compounds. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.042
• 作为产物：
  描述：

  在 iron(III) chloride 、 sodium citrate 、 柠檬酸 、 氨 作用下， 以 水 为溶剂， 反应 0.75h， 生成 5-(3,4-二甲氧基-苯基)-[1,3,4]噻二唑-2-胺
  参考文献：
  名称：

  几种靶向拓扑异构酶ATP结合位点的新型5-溴-2-（5-芳基-1,3,4-噻二唑-2-基）异吲哚啉-1,3-二酮衍生物的合成，对接和生物评价

  摘要：

  人拓扑异构酶IIα（htopoIIα）是设计抗癌药物的公认目标。在各种阻断htopoIIα功能的方法中，针对ATP位点的竞争性抑制作用的研究相对较少。因此，为了鉴定一些靶向ATP结合位点的新型htopoIIα抑制剂，我们设计并合成了一个与沙利度胺结构相关的5-芳基-1,3,4-噻二唑偶联的邻苯二甲酰亚胺衍生物的小文库。最初，通过氯化铁催化硫代半脲酮衍生物（THZ 1-8）的氧化环化反应，合成了2-氨基-5-芳基-1,3,4-噻二唑衍生物（TDZ 1-8），后者是通过取代的芳基反应制得的。醛与硫代氨基脲。TDZ 1-8在4Å分子筛和冰醋酸存在下与4-溴邻苯二甲酸酐反应生成5-溴-2-（5-芳基-1,3,4-噻二唑-2-基）异吲哚啉-1,3 -二酮衍生物（PTD 1-8）。通过IR，1 H-NMR和LCMS对所有合成的化合物进行表征。最终化合物PTD 1-8停靠在htopoIIαB链的ATP结

  DOI：

  10.2174/157018012801319463

文献信息

• Synthesis and anti-inflammatory activity of some new thiadiazole linked pyrazole benzene sulphonamides as cyclooxygenase inhibitors
  作者：Jahangir Alam、Ozair Alam、Rahmat Ali、Mohd Naim、Suroor Khan

  DOI：10.13005/ojc/310404

  日期：2015.12.30

  A new series of thiadiazole linked pyrazole benzenesulfonamide derivatives were synthesized by the condensation of aldehydic pyrazole with aryl substituted thiadiazole amine followed by Schiff base reaction. The synthesized compounds (6a-o) were characterized by IR, NMR, and Mass spectral data, further evaluated their in-vivo anti-inflammatory, analgesic and in-vitro COX-II inhibition assay. The compounds 6b and 6m showed most significant in-vivo anti-inflammatory with 72.33 and 71.17% inhibition along analgesic activity having 67.89% and 71.37 % respectively. Their selectivity against COX-II enzyme with selectivity index 67.81 and 66.38 was established for 6b and 6m, which is compared with Celecoxib. During the gastric ulceration study, selected compounds couldn’t observed any ulcerogenic effect on gastric mucosa.The in-silico pharmacokinetic profile and molecular docking study exposed very good binding affinity towards the cycloxygenase (COX-II) enzyme (PDB Id: 3PGH), therefore the compounds 6b and 6m are used as promising lead candidates for the support of drug development.

  通过醛基吡唑与芳基取代的噻二唑胺缩合，随后进行希夫碱反应，合成了一系列新的噻二唑联吡唑苯磺酰胺衍生物。合成的化合物（6a-o）通过IR、NMR和质谱数据进行表征，并进一步评估了其在体内的抗炎、镇痛作用及体外COX-II抑制活性。化合物6b和6m显示出最显著的体内抗炎活性，抑制率分别为72.33%和71.17%，同时具有镇痛活性，分别为67.89%和71.37%。它们对COX-II酶的选择性指数分别为67.81和66.38，与塞来昔布相比。在胃溃疡研究中，选定的化合物未观察到对胃黏膜的溃疡形成作用。通过计算机模拟的药代动力学特征和分子对接研究显示，这些化合物对环氧合酶（COX-II）酶（PDB ID：3PGH）具有非常好的结合亲和力，因此，化合物6b和6m被视为有前途的先导候选物，用于支持药物开发。
• 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, molecular docking, antimicrobial evaluation, and DNA cleavage assay of new thiadiazole/oxadiazole ciprofloxacin derivatives
  作者：Hamada H. H. Mohammed、Samar H. Abbas、El-Shimaa M. N. Abdelhafez、James M. Berger、Satoshi Mitarai、Masayoshi Arai、Gamal El-Din A. A. Abuo-Rahma

  DOI：10.1007/s00706-019-02478-4

  日期：2019.10

  AbstractHerein we report the synthesis of new N-4-piperazinyl thiadiazole and oxadiazole ciprofloxacin derivatives and their antibacterial and antimycobacterial activities. Although thiadiazole ciprofloxacin derivatives compound showed broad spectrum antibacterial activity against all the tested strains either Gram-positive or Gram-negative organisms, the oxadiazole derivatives exhibited weaker antibacterial

  摘要本文中，我们报道了新的N -4-哌嗪基噻二唑和恶二唑环丙沙星衍生物的合成及其抗菌和抗分枝杆菌活性。尽管噻二唑环丙沙星衍生物化合物对革兰氏阳性或革兰氏阴性菌的所有测试菌株均具有广谱抗菌活性，但与参考环丙沙星相比，恶二唑衍生物对大多数测试菌株的抗菌和分枝杆菌活性较噻二唑衍生物弱。此外，抗分枝杆菌筛选显示含有噻二唑支架的化合物有效抑制耻垢分枝杆菌MIC分别为1.56和3.13，并适度抑制了耐药菌株。DNA裂解分析表明，噻二唑环丙沙星衍生物抑制超螺旋松弛，尽管程度比环丙沙星要小，并且还增加了产生的切口底物的量。 图形摘要
• Synthesis and Antiviral Activity of Novel 1,3,4-Thiadiazole Inhibitors of DDX3X
  作者：Brai、Ronzini、Riva、Botta、Zamperini、Borgini、Trivisani、Garbelli、Pennisi、Boccuto、Saladini、Zazzi、Maga、Botta

  DOI：10.3390/molecules24213988

  日期：——

  emerged as a novel therapeutic target in the fight against both infectious diseases and cancer. Herein, a new family of DDX3X inhibitors was designed, synthesized, and tested for its inhibitory action on the ATPase activity of the enzyme. The potential use of the most promising derivatives it has been investigated by evaluating their anti-HIV-1 effects, revealing inhibitory activities in the low micromolar

  人类 ATPase/RNA 解旋酶 X-linked DEAD-box 多肽 3 (DDX3X) 成为对抗传染病和癌症的新治疗靶点。在此，设计、合成了一个新的 DDX3X 抑制剂家族，并测试了其对该酶的 ATPase 活性的抑制作用。通过评估它们的抗 HIV-1 效果，研究了最有前途的衍生物的潜在用途，揭示了低微摩尔范围内的抑制活性。初步的 ADME 分析表明高代谢稳定性和良好的水溶性。有前途的生物学特征，加上合适的体外药代动力学特性，使这些新化合物成为进一步开发的一个很好的起点。
• Synthesis, characterization and biological evaluation of some novel fluoroquinolones
  作者：Neelanjana Pandit、Kamal Shah、Neetu Agrawal、Neeraj Upmanyu、Sushant K. Shrivastava、Pradeep Mishra

  DOI：10.1007/s00044-016-1526-x

  日期：2016.5

  Different derivatives of fluoroquinolones were synthesized by combining it with different thiadiazoles. The synthesized compounds were characterized by infrared spectroscopy, proton nuclear magnetic resonance and mass spectral data. The compounds were screened for their antibacterial and antifungal activity. Ciprofloxacin derivatives with thiadiazoles 7c showed good antibacterial as well as antifungal

  通过将氟喹诺酮与不同的噻二唑结合，可以合成出不同的氟喹诺酮衍生物。通过红外光谱，质子核磁共振和质谱数据对合成的化合物进行表征。筛选化合物的抗菌和抗真菌活性。环丙沙星衍生物与噻二唑7c表现出良好的抗菌和抗真菌活性，而13c和13e分别表现出抗菌和抗真菌活性。司帕沙星衍生物8c表现出抗菌和抗真菌活性。司帕沙星衍生物14b和14e分别显示出抗菌和抗真菌活性。