methyl 3-[(2-methoxycarbonylethyl)-4-chlorophenylamino]propanoate | 1179812-13-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: methyl 3-[(2-methoxycarbonylethyl)-4-chlorophenylamino]propanoate
• 英文别名: dimethyl 3,3′-(4-chlorophenylazanediyl)dipropanoate；dimethyl 3,3'-(4-chlorophenylazanediyl)dipropanoate；methyl 3-(4-chloro-N-(3-methoxy-3-oxopropyl)anilino)propanoate
• CAS: 1179812-13-5
• 化学式: C₁₄H₁₈ClNO₄
• 分子量: 299.754
• InChiKey: NHNRCSHBGHLLNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  对氯苯胺 、 丙烯酸甲酯（MA） 在 copper(l) chloride 作用下， 以 溶剂黄146 为溶剂， 反应 48.0h， 生成 methyl 3-[(2-methoxycarbonylethyl)-4-chlorophenylamino]propanoate
  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

文献信息

• Synthesis of Bis Azole, Diazole, and Triazole Derivatives from<i>N</i>-(4-Chloro/Iodophenyl)-<i>N</i>-carboxyethyl-β-alanine Dihydrazides
  作者：Kazimieras Anusevicius、Rita Vaickelioniene、Vytautas Mickevicius、Gema Mikulskiene

  DOI：10.1002/jhet.1070

  日期：2013.3

  A new potentially biologically active N‐(4‐chloro/iodophenyl)‐N‐carboxyethyl‐β‐alanine derivatives (2, 2a, 2b, 3, 3a, 3b, 4, 4a, 4b, 8, 8a, 8b, 9, 9a, 9b) and products of their cyclization 6, 6a, 6b, 7, 7a, 7b, 10, 10a, 10b, 11, 11a, 11b were obtained and characterized by the methods of 1H‐NMR, 13C‐NMR, IR, mass spectroscopy, and elemental analysis.

  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。
• [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。
• Solvent-Promoted and -Controlled Aza-Michael Reaction with Aromatic Amines
  作者：Kavita De、Julien Legros、Benoit Crousse、Danièle Bonnet-Delpon

  DOI：10.1021/jo9012699

  日期：2009.8.21

  1,4-Addition of anilines onto Michael acceptors proceeds easily in specific polar protic solvent, without any promoting agent. According to the solvent and to the electrophile, the selectivity of the reaction can be finely tuned. With methyl acrylate as electrophile, only monoaddition takes place in water, while the diadduct is yielded in hexafluoroisopropyl alcohol (HFIP). The use of methyl vinyl ketone as a partner affords the monoadduct in water, the diadduct in trifluoroethanol (TFE), and the quinoline in HFIP.
• 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.