3-硝基-N-(5-硝基-1,3-噻唑-2-基)苯甲酰胺 | 64724-88-5

• 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: 3-硝基-N-(5-硝基-1,3-噻唑-2-基)苯甲酰胺
• 英文名称: 3-nitro-N-(5-nitro-1,3-thiazol-2-yl)benzamide
• 英文别名: 3-nitro-N-(5-nitro-2-thiazolyl)benzamide
• CAS: 64724-88-5
• 化学式: C₁₀H₆N₄O₅S
• 分子量: 294.247
• InChiKey: QFPGKQYYQDTOFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-硝基-N-(5-硝基-1,3-噻唑-2-基)苯甲酰胺 、 2-碘乙酰胺 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 生成 2-[(3-nitrobenzoyl)imino]-5-nitro-4-thiazoline-3-acetamide
  参考文献：
  名称：

  Heterocyclic chemicals, their preparation and use

  摘要：

  式（III）的化合物：##STR1##其中R.sup.5是苯环的2位或3位的单个取代基，在2位时，R.sup.5是氯原子、甲基或硝基；R.sup.6是氢原子或CO.CH.sub.3基团。可以通过类似于已知技术中已知的方法制备这些化合物，例如，通过相应的硝基噻唑基苯甲酰胺与相应的卤代（二）乙酰胺发生反应。式（III）的化合物具有裂体吸虫活性，可以单独使用这种化合物，也可以作为药物配方使用。

  公开号：

  US04379156A1
• 作为产物：
  描述：

  间硝基苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 3-硝基-N-(5-硝基-1,3-噻唑-2-基)苯甲酰胺
  参考文献：
  名称：

  铜绿假单胞菌Ⅲ型分泌系统抑制剂含噻唑芳酰胺衍生物的设计与合成

  摘要：

  为了鉴定食源性病原体铜绿假单胞菌中 III 型分泌系统 (T3SS) 的有效抑制剂，我们通过主动剪接将水杨酸与各种杂环合并，合成了 35 种含噻唑的芳基酰胺。通过筛选exoS启动子活性，我们从这 35 种化合物中发现了一种高效的 T3SS 抑制剂。通过后续实验，证实化合物II-22特异性靶向铜绿假单胞菌的T3SS。此外，化合物II-22通过调节 CyaB-cAMP/Vfr-ExsA 和 ExsCED-ExsA 调节途径抑制效应蛋白 ExoS 的分泌。此外，化合物II-22抑制了针复合体组装相关基因的转录，从而降低了细菌毒力。通过使用大蜡螟幼虫的接种试验进一步验证了化合物II-22的强大体内功效。研究还表明，化合物II-22增强了 CIP（环丙沙星）和 TOB（妥布霉素）等抗生素的杀菌活性。这些结果可能有助于开发新型抗菌药物以降低细菌耐药性。

  DOI：

  10.1021/acs.jafc.4c02277

文献信息

• Synthesis and Antimicrobial Evaluation of Nitazoxanide-Based Analogues: Identification of Selective and Broad Spectrum Activity
  作者：T. Eric Ballard、Xia Wang、Igor Olekhnovich、Taylor Koerner、Craig Seymour、Joseph Salamoun、Michelle Warthan、Paul S. Hoffman、Timothy L. Macdonald

  DOI：10.1002/cmdc.201000475

  日期：2011.2.7

  library composed of nitazoxanide‐based analogues was synthesized and assayed for increased antibacterial efficacy against the pyruvate–ferredoxin oxidoreductase (PFOR) using microorganisms Helicobacter pylori, Campylobacter jejuni and Clostridium difficile. Derivatives were found to recapitulate and improve activity against these organisms and select analogues were tested for their ability to disrupt

  合成了一个由基于硝唑尼特的类似物组成的文库，并使用微生物幽门螺杆菌、空肠弯曲杆菌和艰难梭菌对丙酮酸-铁氧还蛋白氧化还原酶 (PFOR) 的抗菌功效进行了分析。发现衍生物可以概括并提高针对这些生物的活性，并测试了选择的类似物直接破坏 PFOR 酶的能力。该文库还针对葡萄球菌的活性进行了筛选，并鉴定出能够以低微摩尔最低抑制浓度抑制葡萄球菌和所有 PFOR 生物体的类似物，并且对人类包皮细胞的毒性较低。
• Nitrothiazolines, their preparation and pharmaceutical formulations containing them
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0031563A1

  公开（公告）日：1981-07-08

  Compounds of formula (III): wherein R5 is a single substituent in position 2 or 3 of the phenyl ring and when in the 2-position R5 is a chlorine atom, a methyl group or a nitro group and when in the 3-position R5 is a nitro group; and R6 is a hydrogen atom or a CO . CH3 group may be prepared by methods analogous to those known in the art, for example, by reaction of the corresponding nitrothiazolyl benzamide with the corresponding halo(di)acetamide. The compounds of formula (III) have schistosomicidal activity and may be administered either as the compound alone or as a pharmaceutical formulation.

  式(III)化合物： 其中 R5 是位于苯环 2 位或 3 位的单个取代基，当位于 2 位时，R5 是氯原子、甲基或硝基，当位于 3 位时 R5 是硝基；R6 是氢原子或 CO .CH3 基团可通过与本领域已知方法类似的方法制备，例如，相应的硝基噻唑基苯甲酰胺与相应的卤代（二）乙酰胺反应。式(III)化合物具有杀血吸虫活性，可单独或作为药物制剂给药。
• Cavier; Gayral; Guillaumel, European Journal of Medicinal Chemistry, 1978, vol. 13, # 6, p. 539 - 543
  作者：Cavier、Gayral、Guillaumel、et al.

  DOI：——

  日期：——
• LIGANDS THAT TARGET HEPATITIS C VIRUS E2 PROTEIN
  申请人：BALHORN Rodney

  公开号：US20160361311A1

  公开（公告）日：2016-12-15

  Hepatitis C Virus (HCV) infects 200 million individuals worldwide. Although several FDA approved drugs targeting the HCV serine protease and polymerase have shown promising results, there is a need for better drugs that are effective in treating a broader range of HCV genotypes and subtypes without being used in combination with interferon and/or ribavirin. Recently, the crystal structure of the core of the HCV E2 protein (E2c) has been determined, providing structural information that can now be used to target the E2 protein and develop drugs that disrupt the early stages of HCV infection by blocking E2's interaction with different host factors. By targeting sites containing conserved E2 amino acids in the CD81 binding site on HCV E2, one might also be able to develop drugs that block HCV infection in a genotype-independent manner. Using the E2c structure as a template, a structural model of the E2 protein core (residues 421-645) was developed that includes the three amino acid segments that are not present in the E2c crystal structure. Blind docking of a diverse library of 1715 small molecules to this model led to the identification of a set of 34 ligands predicted to bind near conserved amino acid residues involved in the HCV E2:CD81 interaction. Surface plasmon resonance was used to screen the ligand set for binding to recombinant E2 protein, and the best binders were subsequently tested to identify compounds that inhibit the infection of hepatocytes by HCV. One compound, 281816, blocked E2 binding to CD81 and inhibited hepatocyte infection by HCV genotypes 1a, 1b, 2a, 2b, 4a and 6a with IC50's ranging from 2.2 μM to 4.6 μM. Methods are described for preventing or treating HCV infection using small molecule inhibitors such as 281816 that target E2 and disrupt its interactions.
• US4379156A
  申请人：——

  公开号：US4379156A

  公开（公告）日：1983-04-05