N'-(3-nitrobenzylidene)benzenesulfonohydrazide | 35559-18-3

• 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: N'-(3-nitrobenzylidene)benzenesulfonohydrazide
• 英文别名: benzenesulfonic acid-(3-nitro-benzylidenehydrazide)；Benzolsulfonsaeure-(3-nitro-benzylidenhydrazid)；N-[(3-nitrophenyl)methylideneamino]benzenesulfonamide
• CAS: 35559-18-3
• 化学式: C₁₃H₁₁N₃O₄S
• 分子量: 305.314
• InChiKey: SKRKKLVWIJOXCD-UHFFFAOYSA-N

物化性质

• 熔点：
  190-191 °C (decomp)
• 沸点：
  491.7±47.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N'-(3-nitrobenzylidene)benzenesulfonohydrazide 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， -15.0~20.0 ℃ 、300.01 kPa 条件下， 反应 1.0h， 生成 N-(3-(2-(4-methoxyphenyl)-2H-tetrazol-5-yl)phenyl)-4-(trifluoromethyl)benzamide
  参考文献：
  名称：

  Structure activity relationships, multidrug resistance reversal and selectivity of heteroarylphenyl ABCG2 inhibitors

  摘要：

  An overexpression of the transmembrane ATP-binding cassette transporter G2 (ABCG2, BCRP) in cancer tissues is supposed to play a role in the multidrug resistance (MDR) of tumors resulting in an inefficient chemotherapy. Therefore, co-administration of selective and non-toxic ABCG2 inhibitors is a promising strategy for improving the efficacy of chemotherapy by blocking ABCG2-mediated export of the cytostatic drugs. In the present study, we designed a small library of 38 novel compounds containing a heteroaryl-phenyl scaffold possessing several (bioisosteric) moieties, and twelve new precursors. We investigated the library for ABCG2 inhibition, for the selectivity against MDR-involved efflux pump ABCBI (P-gp) and for toxicity. Structure activity relationship (SAR) studies revealed that, at least a phenylheteroaryl-phenylamide scaffold is necessary for observing an ABCG2 inhibition. 4-Methoxy-N-(2(2-(6-methoxypyridin-3-yl)-2H-tetrazol-5-yl)phenyl)benzamide (43) exhibited a high potency (IC50 = 61 nM)), selectivity, low intrinsic toxicity and reversed the ABCG2-mediated drug resistance in presence of only 0.1 mu M. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.01.012
• 作为产物：
  描述：

  间硝基苯甲醛 、 苯磺酰肼 以 四氢呋喃 为溶剂， 生成 N'-(3-nitrobenzylidene)benzenesulfonohydrazide
  参考文献：
  名称：

  苯磺酰肼基噻唑并恶嗪稠杂环衍生物的合成、表征及抗菌活性

  摘要：

  使用各种苯甲醛衍生物制备苯磺酰肼（SBSZ）（1a-e）的席夫碱。(1a-e)SBSZ 然后与巯基乙酸缩合。然后将得到的2-噻唑烷酮衍生物(2a-e)与5-硝基-2糠拉啶衍生物即(Z)-N-(5-((5-硝基呋喃-2-基)亚甲基)-4-氧代-2缩合-取代的噻唑烷-3-基)苯磺酰胺(3a-e)。这些衍生物进一步与苯基脲缩合，得到稠合杂环衍生物，即 N-(2-取代-7-(5-硝基呋喃-2-基)-5-(苯基氨基)-2H-噻唑并[5,4-e] [ 1,3]恶嗪-3(3aH)-基)苯磺酰胺(4a-e)。所有衍生物均通过C、H、N元素分析仪和IR-NMR-MS进行了表征。针对选定的常见微生物，研究了所有衍生物的抗菌特性。所有三个系列(即2a-e、3a-e和4a-e)化合物的抗菌活性结果表明所有化合物对细菌都有毒。然而，含氯化合物比其他化合物毒性更大。

  DOI：

  10.13005/ojc/390323

文献信息

• Colautti,A. et al., Chimica Therapeutica, 1971, vol. 6, p. 367 - 379
  作者：Colautti,A. et al.

  DOI：——

  日期：——
• Structure activity relationships, multidrug resistance reversal and selectivity of heteroarylphenyl ABCG2 inhibitors
  作者：Sebastian C. Köhler、Sahel Vahdati、Matthias S. Scholz、Michael Wiese

  DOI：10.1016/j.ejmech.2018.01.012

  日期：2018.2

  An overexpression of the transmembrane ATP-binding cassette transporter G2 (ABCG2, BCRP) in cancer tissues is supposed to play a role in the multidrug resistance (MDR) of tumors resulting in an inefficient chemotherapy. Therefore, co-administration of selective and non-toxic ABCG2 inhibitors is a promising strategy for improving the efficacy of chemotherapy by blocking ABCG2-mediated export of the cytostatic drugs. In the present study, we designed a small library of 38 novel compounds containing a heteroaryl-phenyl scaffold possessing several (bioisosteric) moieties, and twelve new precursors. We investigated the library for ABCG2 inhibition, for the selectivity against MDR-involved efflux pump ABCBI (P-gp) and for toxicity. Structure activity relationship (SAR) studies revealed that, at least a phenylheteroaryl-phenylamide scaffold is necessary for observing an ABCG2 inhibition. 4-Methoxy-N-(2(2-(6-methoxypyridin-3-yl)-2H-tetrazol-5-yl)phenyl)benzamide (43) exhibited a high potency (IC50 = 61 nM)), selectivity, low intrinsic toxicity and reversed the ABCG2-mediated drug resistance in presence of only 0.1 mu M. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Synthesis, Characterization and Antimicrobial Activity of Thiazolo-oxazine Fused Heterocyclic Derivatives, Based on Benzene Sulfonyl Hydrazide
  作者：Saisuryanarayana Donthukurthi、Devdatt J Patel、Rakesh I. Patel、Piyush J. Vyas

  DOI：10.13005/ojc/390323

  日期：2023.6.30

  benzaldehyde derivatives. (1a-e) SBSZ were then condensed with mercapto acetic acid. The obtained resultant 2-thiazolidinone derivatives (2a-e) were then condensed with 5-nitro-2furfuralidine derivatives i.e. (Z)-N-(5-((5-nitrofuran-2-yl) methylene)-4-oxo-2-substitutedthiazolidin-3-yl) benzenesulfonamide (3a-e). These derivatives were further condensed with phenyl urea to yield fused heterocyclic derivatives

  使用各种苯甲醛衍生物制备苯磺酰肼（SBSZ）（1a-e）的席夫碱。(1a-e)SBSZ 然后与巯基乙酸缩合。然后将得到的2-噻唑烷酮衍生物(2a-e)与5-硝基-2糠拉啶衍生物即(Z)-N-(5-((5-硝基呋喃-2-基)亚甲基)-4-氧代-2缩合-取代的噻唑烷-3-基)苯磺酰胺(3a-e)。这些衍生物进一步与苯基脲缩合，得到稠合杂环衍生物，即 N-(2-取代-7-(5-硝基呋喃-2-基)-5-(苯基氨基)-2H-噻唑并[5,4-e] [ 1,3]恶嗪-3(3aH)-基)苯磺酰胺(4a-e)。所有衍生物均通过C、H、N元素分析仪和IR-NMR-MS进行了表征。针对选定的常见微生物，研究了所有衍生物的抗菌特性。所有三个系列(即2a-e、3a-e和4a-e)化合物的抗菌活性结果表明所有化合物对细菌都有毒。然而，含氯化合物比其他化合物毒性更大。