3,3′-(phenylazanediyl)dipropanehydrazide | 56329-74-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,3′-(phenylazanediyl)dipropanehydrazide
• 英文别名: 3,3'-(phenylazanediyl)di(propanehydrazide)；N-Phenyliminodipropionsaeuredihydrazid；3,3'-(Phenylimino)bispropanehydrazide；3-(N-(3-hydrazinyl-3-oxopropyl)anilino)propanehydrazide
• CAS: 56329-74-9
• 化学式: C₁₂H₁₉N₅O₂
• 分子量: 265.315
• InChiKey: ZRGRYZFXCUVRMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  114
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,3′-(phenylazanediyl)dipropanehydrazide 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 4-phenyl-3-(2-{[2-(4-phenyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)ethyl]anilino}ethyl)-4,5-dihydro-1H-1,2,4-triazol-5-thione
  参考文献：
  名称：

  1，（3,4-氧杂（噻）二唑，1,2,4-三唑-5-（硫代）酮和3-（（2-羧乙基）苯基氨基）丙酸的 S- 取代衍生物的合成及生物活性

  摘要：

  摘要 合成了一系列带有两个相同取代的1,3,4-恶二唑，1,3,4-噻二唑或1,2,4-三唑部分的3-（（2-羧乙基）苯基氨基）丙酸新衍生物并通过IR，1 H，13 C NMR光谱和元素分析数据证实了它们的分子结构。筛选合成的化合物的还原能力，清除自由基，调节植物生长和抗菌性能。5,5'-（（（苯基氮杂二基）双（乙烷-2,1-二基））双（4-苯基-2,4-二氢-3 H -1,2,4-三唑-3-硫酮）显示出优异的抗氧化剂活性，是抗生素对照（头孢唑啉）的三倍。2,2'-（（（（（（苯基氮杂二烷基）双（乙烷-2,1-二基））双（4-苯基-4 H -1,2,4-三唑-5,3-二基））双（磺酰二基）二乙酸盐对 铜绿假单胞菌 具有显着的杀菌活性 ，MBC和MIC值为7.3 µg / ml，而12种化合物对 白色念珠菌 具有显着的杀菌活性 。 MIC值为3.9 µg / ml。 图形摘要 化合物的合成 2

  DOI：

  10.1007/s11164-015-2290-0
• 作为产物：
  描述：

  N,N-二甲氧基羰基乙基苯胺 在 一水合肼 作用下， 以 异丙醇 为溶剂， 反应 48.0h， 以72%的产率得到3,3′-(phenylazanediyl)dipropanehydrazide
  参考文献：
  名称：

  Synthesis and Quantitative Structure–Activity Relationship of Imidazotetrazine Prodrugs with Activity Independent of O6-Methylguanine-DNA-methyltransferase, DNA Mismatch Repair, and p53

  摘要：

  The antitumor prodrug temozolomide is compromised by its dependence for activity on DNA mismatch repair (MMR) and the repair of the chemosensitive DNA lesion, O6-methylguanine (O6-MeG), by O6-methylguanine-DNA-methyltransferase (E.C. 2.1.1.63, MGMT). Tumor response is also dependent on wild-type p53. Novel 3-(2-anilinoethyl)-substituted imidazotetrazines are reported that have activity independent of MGMT, MMR, and p53. This is achieved through a switch of mechanism so that bioactivity derives from imidazotetrazine-generated arylaziridinium ions that principally modify guanine-N7 sites on DNA. Mono- and bifunctional analogues are reported, and a quantitative structure-activity relationship (QSAR) study identified the p-tolyl-substituted bifunctional congener as optimized for potency, MGMT-independence, and MMR-independence. NCI60 data show the tumor cell response is distinct from other imidazotetrazines and DNA-guanine-N7 active agents such as nitrogen mustards and cisplatin. The new imidazotetrazine compounds are promising agents for further development, and their improved in vitro activity validates the principles on which they were designed.

  DOI：

  10.1021/jm401121k

文献信息

• [EN] AMINOALYL-IMIDAZOTETRAZINES FOR TREATMENT OF CANCER<br/>[FR] AMINOALLYLIMIDAZOTÉTRAZINES POUR LE TRAITEMENT DE CANCERS
  申请人：UNIV BRADFORD

  公开号：WO2009127815A1

  公开（公告）日：2009-10-22

  The present invention relates to imidazotetrazines of Formula (I) and their use in the treatment of cancer.

  本发明涉及式(I)的咪唑四嗪及其在治疗癌症中的用途。
• Novel N-Substituted Amino Acid Hydrazone-Isatin Derivatives: Synthesis, Antioxidant Activity, and Anticancer Activity in 2D and 3D Models In Vitro
  作者：Ingrida Tumosienė、Ilona Jonuškienė、Kristina Kantminienė、Vytautas Mickevičius、Vilma Petrikaitė

  DOI：10.3390/ijms22157799

  日期：——

  or diphenylamine fragments were synthesized, and their anticancer activities were tested by MTT assay against human melanoma A375 and colon adenocarcinoma HT-29 cell lines. In general, the synthesized compounds were more cytotoxic against HT-29 than A375. 3-((4-Methoxyphenyl)(3-oxo-3-(2-(2-oxoindolin-3-ylidene)hydrazinyl)propyl)amino)-N’-(2-oxoindolin-3-ylidene)propanehydrazide and (N’,N’’’)-1,1’-(methylenebis(4

  合成了一系列新的单腙和双腙，每个都带有 2-羟吲哚部分以及取代的苯氨基丙酰胺、吡咯烷-2-one、苯并咪唑、二苯甲烷或二苯胺片段，并通过 MTT 法测试了它们对人黑色素瘤 A375 和结肠的抗癌活性腺癌 HT-29 细胞系。一般来说，合成的化合物对 HT-29 的细胞毒性比 A375 更强。3-((4-甲氧基苯基)(3-oxo-3-(2-(2-oxoindolin-3-ylidene)hydrazinyl)丙基)amino) -N '-(2-oxoindolin-3-ylidene)丙酰肼和( N ', N ''')-1,1'-(亚甲基双(4,1-亚苯基))双(5-氧代-N'-(2-oxoindolin-3-ylidene)pyrrolidine-3-carbohydrazide) 被鉴定为在 2D 和 3D 细胞培养物中对抗 HT-29 的最活性化合物。在通过铁还原抗氧化能力测定 (FRAP)
• POLYACETAL RESIN COMPOSITION
  申请人：Polyplastics Co., Ltd.

  公开号：EP1686156A1

  公开（公告）日：2006-08-02

  A polyacetal resin composition comprises a polyacetal resin and a hetero atom-containing aliphatic carboxylic acid hydrazide. The proportion of the hetero atom-containing aliphatic carboxylic acid hydrazide may be about 0.001 to 20 parts by weight relative to 100 parts by weight of the polyacetal resin. The polyacetal resin composition may further comprise at least one member selected from the group consisting of an antioxidant, a heat stabilizer, a processing stabilizer, a weather (light)-resistant stabilizer, an impact resistance improver, a gloss control agent, an agent for improving sliding property, a coloring agent, and a filler. Such a resin composition improves stability of the polyacetal resin and inhibits formaldehyde emission.

  聚缩醛树脂组合物由聚缩醛树脂和含杂原子的脂肪族羧酸酰肼组成。相对于 100 重量份的聚缩醛树脂，含杂原子的脂肪族羧酸酰肼的比例可为 0.001 至 20 重量份。聚缩醛树脂组合物可进一步包含至少一种选自以下组别的成员：抗氧化剂、热稳定剂、加工稳定剂、耐候（光）稳定剂、抗冲击性改进剂、光泽控制剂、改善滑动性能剂、着色剂和填料。这种树脂组合物可以提高聚缩醛树脂的稳定性，并抑制甲醛释放。
• Yao, Ri-Sheng; Jiang, Lai-En; Wu, Sheng-Hua, Asian Journal of Chemistry, 2011, vol. 23, # 9, p. 3792 - 3794
  作者：Yao, Ri-Sheng、Jiang, Lai-En、Wu, Sheng-Hua、Deng, Sheng-Song、Yang, Yang

  DOI：——

  日期：——
• Synthesis of azoles from 3-[(3-hydrazino-3-oxopropyl)anilino]-and 3-[(3-hydrazino-3-oxopropyl)-4-methylanilino]propane hydrazides
  作者：I. Tumosiene、Z. I. Beresnevicius

  DOI：10.1007/s10593-007-0176-9

  日期：2007.9