2-acetylpyridine-para-hydroxyphenylhydrazone

• 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: 2-acetylpyridine-para-hydroxyphenylhydrazone
• 英文别名: 4-hydroxy-N-(1-pyridin-2-ylethylideneamino)benzamide
• 化学式: C₁₄H₁₃N₃O₂
• 分子量: 255.276
• InChiKey: SGBUGDYZFHACQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  水 、 三氯化锑 、 2-acetylpyridine-para-hydroxyphenylhydrazone 以 甲醇 为溶剂， 反应 4.0h， 以81%的产率得到[2-acetylpyridine-para-hydroxyphenylhydrazonato(dichloro)antimony(III)] hemihydrate
  参考文献：
  名称：

  Effect of coordination to antimony(III) on the antifungal activity of 2-acetylpyridine- and 2-benzoylpyridine-derived hydrazones

  摘要：

  Antimony(III) [Sb(L)Cl-2] complexes were obtained with 2-acetylpyridine-phenylhydrazone (H2AcPh), 2-acetylpyridine-para-chloro-phenylhydrazone (H2AcpClPh), 2-acetylpyridine-para-nitro-phenylhydrazone (H2AcpNO(2)Ph) and 2-acetylpyridine-para-hydroxy-phenylhydrazone (H2AcpOHPh) along with the 2-benzoylpyridine-phenylhydrazone analogs H2BzPh, H2BzpClPh, H2BzpNO(2)Ph, H2BzpOHPh (HL). [Sb(2BzpClPh)Cl-2], complex (6), (IC50 = 4.91 +/- 1.20 mu mol L-1) was as active as nystatin (IC50= 4.44 +/- 0.76 mu mol L-1) and twofold more active than H2BzpClPh (IC50= 10.05 +/- 0.67 mu mol L-1) against Candida dubliniensis. While H2BzpClPh proved to be inactive against Candida glabrata, 6 (IC50 = 10.11 +/- 0.64 mu mol L-1) was more active than miconazole nitrate (IC50= 19.50 +/- 4.53 mu mol L-1). Similarly, H2BzpNO(2)Ph revealed to be inactive against Candida lusitaniae whereas complex [Sb(2BzpNO(2)Ph)Cl-2] (7) (IC50 = 8.54 +/- 2.21 mu mol L-1) proved to be as active as nystatin (IC50 = 5.31 +/- 0.84 mu mol L-1). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2015.05.004
• 作为产物：
  描述：

  2-乙酰基吡啶 、 4-羟基苯甲酰肼 以 1,2-丙二醇 、 二甲基亚砜 为溶剂， 生成 2-acetylpyridine-para-hydroxyphenylhydrazone
  参考文献：
  名称：

  Screening a small hydrazide-hydrazone combinatorial library for targeting the STAT3 in monocyte-macrophages with insulated reporter transposons

  摘要：

  摘要 信号转导和转录激活因子3（STAT3）药物靶向被认为是治疗癌症、自身免疫性疾病或炎症性疾病的一种前瞻性方法。我们开发了一系列STAT3、NF-κB、Nrf2、金属反应性转录因子-1（MTF-1）和缺氧诱导因子1α（HIF-1α）在人单核-巨噬细胞系THP-1中转录激活的报告基因。这些报告基因被用来测试一组作为潜在 STAT3 抑制剂的酰肼。由 7 个羰基成分和 10 个酰肼成分的 70 个二元组合组成的酰肼-酰腙库，包括 STAT3 抑制剂临床药物硝呋沙齐，已经组装完成并通过报告基因筛选。就整个库而言，在 THP-1 单核细胞中发现 STAT3 和 NF-κB 或 STAT3 和 HIF-1α 报告物的反应之间存在明显的相关性。针对选定的抑制组合，制备了相应的酰肼，并进行了单独测试。在 THP-1 细胞中，最有效的 2-乙酰基吡啶-4-氯苯甲酰腙对 STAT3 的抑制潜力明显超过硝呋沙齐（ED50 分别为 2 和 50 μM）。我们的结论是，绝缘报告转座子可能是药物发现应用的有用工具。 图表摘要

  DOI：

  10.1007/s00044-023-03028-8

文献信息

• Bismuth(III) complexes with 2-acetylpyridine- and 2-benzoylpyridine-derived hydrazones: Antimicrobial and cytotoxic activities and effects on the clonogenic survival of human solid tumor cells
  作者：Isabella P. Ferreira、Elisa D.L. Piló、Angel A. Recio-Despaigne、Jeferson G. Da Silva、Jonas P. Ramos、Lucas B. Marques、Pedro H.D.M. Prazeres、Jacqueline A. Takahashi、Elaine M. Souza-Fagundes、Willian Rocha、Heloisa Beraldo

  DOI：10.1016/j.bmc.2016.05.007

  日期：2016.7

  Complexes [Bi(2AcPh)Cl-2]center dot 0.5H(2)O (1), [Bi(2AcpClPh)Cl-2] (2), [Bi(2AcpNO(2)Ph)Cl-2] (3), [Bi(2AcpOHPh)Cl-2]center dot 2H(2)O (4), [Bi(H2BzPh)Cl-3]center dot 2H(2)O (5), [Bi(H2BzpClPh)Cl-3] (6), [Bi(2BzpNO(2)Ph)Cl-2]center dot 2H(2)O (7) and [Bi(H2BzpOHPh)Cl-3]center dot 2H(2)O (8) were obtained with 2-acetylpyridine phenylhydrazone (H2AcPh), its -para-chloro-phenyl-(H2AcpClPh), -para-nitro-phenyl (H2AcpNO(2)Ph) and -para-hydroxy-phenyl (H2AcpOHPh) derivatives, as well as with the 2-benzoylpyridine phenylhydrazone analogues (H2BzPh, H2BzpClPh, H2BzpNO(2)Ph, H2BzpOHPh).Upon coordination to bismuth(III) antibacterial activity against Gram-positive and Gram-negative bacterial strains significantly improved except for complex (4).The cytotoxic effects of the compounds under study were evaluated on HL-60, Jurkat and THP-1 leukemia, and on MCF-7 and HCT-116 solid tumor cells, as well as on non-malignant Vero cells. In general, 2-acetylpyridine-derived hydrazones proved to be more potent and more selective as cytotoxic agents than the corresponding 2-benzoylpyridine-derived counterparts.Exposure of HCT-116 cells to H2AcpClPh, H2AcpNO(2)Ph and complex (3) led to 99% decrease of the clonogenic survival. The IC50 values of these compounds were three-fold smaller when cells were cultured in soft-agar (3D) than when cells were cultured in monolayer (2D), suggesting that they constitute interesting scaffolds, which should be considered in further studies aiming to develop new drug candidates for the treatment of colon cancer. (C) 2016 Elsevier Ltd. All rights reserved.
• Dynamic Acylhydrazone Metal Ion Complex Libraries: A Mixed–Ligand Approach to Increased Selectivity in Extraction
  作者：Seema Choudhary、Janet R. Morrow

  DOI：10.1002/1521-3773(20021104)41:21<4096::aid-anie4096>3.0.co;2-0

  日期：2002.11.4