3-[4-chloro(3-hydrazino-3-oxopropyl)anilino]propanohydrazide | 1190761-96-6

• 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-[4-chloro(3-hydrazino-3-oxopropyl)anilino]propanohydrazide
• 英文别名: 3,3′-(4-chlorophenylazanediyl)dipropanehydrazide；3,3'-((4-chlorophenyl)azanediyl)di(propanehydrazide)；3-(4-chloro-N-(3-hydrazinyl-3-oxopropyl)anilino)propanehydrazide
• CAS: 1190761-96-6
• 化学式: C₁₂H₁₈ClN₅O₂
• 分子量: 299.76
• InChiKey: ZHEKLDKZDCIGJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 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-[4-chloro(3-hydrazino-3-oxopropyl)anilino]propanohydrazide 在 盐酸 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 3,3'-((4-chlorophenyl)azanediyl)dipropionyl azide
  参考文献：
  名称：

  [EN] AMINOALYL-IMIDAZOTETRAZINES FOR TREATMENT OF CANCER
  [FR] AMINOALLYLIMIDAZOTÉTRAZINES POUR LE TRAITEMENT DE CANCERS

  摘要：

  本发明涉及式(I)的咪唑四嗪及其在治疗癌症中的用途。

  公开号：

  WO2009127815A1
• 作为产物：
  描述：

  methyl 3-[(2-methoxycarbonylethyl)-4-chlorophenylamino]propanoate 在 hydrazine hydrate 作用下， 以 异丙醇 为溶剂， 反应 1.0h， 以80%的产率得到3-[4-chloro(3-hydrazino-3-oxopropyl)anilino]propanohydrazide
  参考文献：
  名称：

  由N-（4-氯/碘苯基）-N-羧乙基-β-丙氨酸二酰肼合成双氮唑，二唑和三唑衍生物

  摘要：

  一种新的潜在的生物活性ñ - （4-氯/碘苯基） - ñ羧-β丙氨酸衍生物（2，图2a，图2b，3，图3a，图3b，4，图4a，图4b，8，图8A，8B，9，图9a，图9b）和产品其环化6，图6a，图6b，7，图7a，图7b，10，图10A，10B，11，11A，11B获得并且其特征在于所述方法1 H-NMR，13 C-NMR，IR，质谱和元素分析。

  DOI：

  10.1002/jhet.1070

文献信息

• 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)
• Synthesis and Quantitative Structure–Activity Relationship of Imidazotetrazine Prodrugs with Activity Independent of <i>O</i>6-Methylguanine-DNA-methyltransferase, DNA Mismatch Repair, and p53
  作者：Dimitrios Pletsas、Elrashied A. E. Garelnabi、Li Li、Roger M. Phillips、Richard T. Wheelhouse

  DOI：10.1021/jm401121k

  日期：2013.9.12

  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.