2-(3-Iodoanilino)-1,7-dihydropurin-6-one | 142580-99-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 2-(3-Iodoanilino)-1,7-dihydropurin-6-one
• 英文别名: 2-(3-iodoanilino)-1,7-dihydropurin-6-one
• CAS: 142580-99-2
• 化学式: C₁₁H₈IN₅O
• 分子量: 353.122
• InChiKey: GFOFATATHOMCEM-UHFFFAOYSA-N

物化性质

• 密度：
  2.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴次黄嘌呤 、 3-碘苯胺 以 乙二醇甲醚 为溶剂， 以35%的产率得到2-(3-Iodoanilino)-1,7-dihydropurin-6-one
  参考文献：
  名称：

  N2-苯基鸟嘌呤作为单纯疱疹病毒胸苷激酶抑制剂的定量构效关系。

  摘要：

  已开发出Hansch型的定量构效关系，以解释N2-苯基鸟嘌呤对1型和2型单纯疱疹病毒（HSV1,2）的胸苷激酶的抑制作用。在苯环上具有间和/或对位取代基的衍生物作为酶抑制剂表现出很大范围的重叠，但不完全相同。使用36种（HSV1）和35种抑制剂（HSV2）的IC50值来开发使用疏水（pi），电子（sigma，R）和组大小（MR）参数的方程式。对于1型和2型酶的抑制剂，分别获得了相关系数为0.797和0.805的方程式1和2。电位与间取代基的pi值正相关，而与苯环中对位取代基的pi值负相关。通过对位取代基的共振参数R和间位取代基的σ常数也获得正相关。两种酶中最有效的抑制剂是N2- [间-（三氟甲基）苯基]鸟嘌呤，尽管HSV2胸苷激酶比HSV1酶对某些化合物更敏感。

  DOI：

  10.1021/jm00094a007

文献信息

• USE OF DIANHYDROGALACTITOL OR DERIVATIVES OR ANALOGS THEREOF FOR TREATMENT OF PEDIATRIC CENTRAL NERVOUS SYSTEM MALIGNANCIES
  申请人：BACHA Jeffrey A.

  公开号：US20190175541A1

  公开（公告）日：2019-06-13

  The use of dianhydrogalactitol provides a novel therapeutic modality for the treatment of malignancies of the central nervous system in pediatric patients, including glioblastoma multiforme (GBM) high grade glioma, and medulloblastoma. Dianhydrogalactitol acts as an alkylating agent on DNA that creates N 7 methylation and that can induce double-stranded breaks in DNA. Dianhydrogalactitol is effective in suppressing the growth of cancer stem cells and is active against tumors that are refractory to temozolomide, cisplatin, and tyrosine kinase inhibitors; the drug acts independently of the MGMT repair mechanism. Dianhydrogalactitol can be used together with other anti-neoplastic agents (e.g. cisplatin) and can possess additive or super-additive effects.
• [EN] USE OF DIANHYDROGALACTITOL OR DERIVATIVES AND ANALOGS THEREOF FOR TREATMENT OF NON-SMALL-CELL LUNG CARCINOMA, GLIOBLASTOMA, AND OVARIAN CARCINOMA BY INDUCTION OF DNA DAMAGE AND STALLING OF CELL CYCLE<br/>[FR] UTILISATION DE DIANHYDROGALACTITOL OU DE DÉRIVÉS ET D'ANALOGUES DE CELUI-CI POUR LE TRAITEMENT D'UN CARCINOME NON À PETITES CELLULES, D'UN GLIOBLASTOME ET D'UN CARCINOME DE L'OVAIRE PAR INDUCTION DE LÉSIONS DE L'ADN ET BLOCAGE DU CYCLE CELLULAIRE
  申请人：DEL MAR PHARMACEUTICALS

  公开号：WO2017042634A2

  公开（公告）日：2017-03-16

  The use of dianhydrogalactitol provides a novel therapeutic modality for the treatment of glioblastoma, non-small-cell lung carcinoma (NSCLC) and ovarian cancer, as well as other types of malignancy, including brain metastases of NSCLC. Dianhydrogalactitol acts as an alkylating agent on DNA that creates N7 methylation and inter-strand crosslinks that can induce double-stranded breaks in DNA. Dianhydrogalactitol is effective in suppressing the growth of cancer stem cells and is active against tumors that are refractory to temozolomide, cisplatin, and tyrosine kinase inhibitors; the drug acts independently of the MGMT repair mechanism. Dianhydrogalactitol can be used together with other anti-neoplastic agents and can possess additive or synergistic effects. Dianhydrogalactitol can be used for treatment of leptomeningeal carcinomatosis.
• [EN] USE OF DIANHYDROGALACTITOL OR DERIVATIVES OR ANALOGS THEREOF FOR TREATMENT OF PEDIATRIC CENTRAL NERVOUS SYSTEM MALIGNANCIES<br/>[FR] UTILISATION DE DIANHYDROGALACTITOL OU DES DÉRIVÉS OU ANALOGUES DE CELUI-CI POUR LE TRAITEMENT DE TUMEURS MALIGNES DU SYSTÈME NERVEUX CENTRAL PÉDIATRIQUE
  申请人：DELMAR PHARMACEUTICALS INC

  公开号：WO2017075052A1

  公开（公告）日：2017-05-04

  The use of dianhydrogalactitol provides a novel therapeutic modality for the treatment of malignancies of the central nervous system in pediatric patients, including glioblastoma multiforme (GBM) high grade glioma, and medulloblastoma. Dianhydrogalactitol acts as an alkylating agent on DNA that creates N7 methylation and that can induce double-stranded breaks in DNA. Dianhydrogalactitol is effective in suppressing the growth of cancer stem cells and is active against tumors that are refractory to temozolomide, cisplatin, and tyrosine kinase inhibitors; the drug acts independently of the MGMT repair mechanism. Dianhydrogalactitol can be used together with other anti-neoplastic agents (e.g. cisplatin) and can possess additive or super-additive effects.
• Quantitative structure-activity relationships of N2-phenylguanines as inhibitors of Herpes simplex virus thymidine kinases
  作者：Joseph Gambino、Federico Focher、Catherine Hildebrand、Giovanni Maga、Timothy Noonan、Silvio Spadari、George Wright

  DOI：10.1021/jm00094a007

  日期：1992.8

  (HSV2) were used to develop equations using hydrophobic (pi), electronic (sigma, R), and group size (MR) parameters. Equations 1 and 2 with correlation coefficients of 0.797 and 0.805, respectively, were obtained for inhibitors of the types 1 and 2 enzymes. Potencies were correlated positively with pi values of meta substituents but negatively with pi values of para substituents in the phenyl ring. Positive

  已开发出Hansch型的定量构效关系，以解释N2-苯基鸟嘌呤对1型和2型单纯疱疹病毒（HSV1,2）的胸苷激酶的抑制作用。在苯环上具有间和/或对位取代基的衍生物作为酶抑制剂表现出很大范围的重叠，但不完全相同。使用36种（HSV1）和35种抑制剂（HSV2）的IC50值来开发使用疏水（pi），电子（sigma，R）和组大小（MR）参数的方程式。对于1型和2型酶的抑制剂，分别获得了相关系数为0.797和0.805的方程式1和2。电位与间取代基的pi值正相关，而与苯环中对位取代基的pi值负相关。通过对位取代基的共振参数R和间位取代基的σ常数也获得正相关。两种酶中最有效的抑制剂是N2- [间-（三氟甲基）苯基]鸟嘌呤，尽管HSV2胸苷激酶比HSV1酶对某些化合物更敏感。