2,4-二氨基-6-氯嘧啶-5-甲醛 | 18740-20-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2,4-二氨基-6-氯嘧啶-5-甲醛
• 英文名称: 2,4-diamino-6-chloropyrimidine-5-carbaldehyde
• 英文别名: 2,4-Diamino-6-chlor-pyrimidin-carbaldehyd-(5)
• CAS: 18740-20-0
• 化学式: C₅H₅ClN₄O
• 分子量: 172.574
• InChiKey: FJRYLFSXNGBELH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4-二氨基-6-氯嘧啶-5-甲醛 在 sodium hydrogensulfide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以65%的产率得到2,6-diamino-4-sulfanylidene-1H-pyrimidine-5-carbaldehyde
  参考文献：
  名称：

  Clark, J.; Shahhet, M. S.; Korakas, D., Journal of Heterocyclic Chemistry, 1993, vol. 30, # 4, p. 1065 - 1072

  摘要：

  DOI：

文献信息

• Synthesis of 2,4-diaminothieno- and pyrrolo[2,3-<i>d</i>]pyrimidine-6-carboxylic acid derivatives
  作者：S. Tumkevicius、M. Dailide、A. Kaminskas

  DOI：10.1002/jhet.5570430630

  日期：2006.11

  respectively. Compounds 2a,b by treatment with bases cyclised to the corresponding 2-amino-4-chlorothieno- and pyrrolo[2,3-d]pyrimidine-6-carboxylates (3a,b). Heating 2,4-diamino-6-chloropyrimidine-5-carbaldehyde (5) with ethyl mercaptoacetate or methyl N-methylglycinate gave 2,4-diaminothieno[2,3-d]- and 2,4-diaminopyrrolo[2,3-d]-pyrimidine-6-carboxylates (6a,b), whereas compound 5 with ethyl glycinate

  合成了一系列新的2，4-二氨基噻吩并[2，3- d ]-和2，4-二氨基吡咯并[2，3- d ]嘧啶衍生物。2-氨基-4,6-二氯嘧啶-5-甲醛（1）与巯基乙酸乙酯，N-甲基甘氨酸甲酯或甘氨酸乙酯反应，得到（2-氨基-4-氯-5-甲酰基嘧啶-6-基）硫代乙酸乙酯（2a），N-（2-氨基-4-氯-5-甲酰基嘧啶-6-基）-N-甲基甘氨酸盐（2b）和N-（2-氨基-4-氯-5-甲酰基嘧啶-6-基） ）甘氨酸盐（2c）。化合物2a，b通过用环化成相应的2-氨基-4-氯噻吩并吡咯并[2，3 - d ]嘧啶-6-羧酸盐（3a，b）的碱处理。用巯基乙酸乙酯或N-甲基甘氨酸甲酯加热2,4-二氨基-6-氯嘧啶-5-甲醛（5）得到2,4-二氨基噻吩并[2,3- d ]-和2,4-二氨基吡咯并[2,3- d ]-嘧啶-6-羧酸盐（6a，b），而化合物5与甘氨酸乙酯在相同反应条件下得到N-（2，4-二氨基-5-
• Substituted O6-benzyl-8-aza-guanines
  申请人：The Government of the United States of America, Department of Health and Human Services

  公开号：US20020013299A1

  公开（公告）日：2002-01-31

  The present invention provides AGT inactivating compounds such as substituted O 6 -benzylguanines of the formula 1 7- or 9-substituted 8-aza-O 6 -benzylguanines, 7,8-disubstituted O 6 -benzylguanines, 7,9-disubstituted O 6 -benzylguanines, 4(6)-substituted 2-amino-5-nitro-6 (4) -benzyloxypyrimidines, and 4 (6) -substituted 2-amino-5-nitroso-6(4)-benzyloxypyrimidines, as well as pharmaceutical compositions comprising such compounds along with a pharmaceutically acceptable carrier. The present invention further provides a method of enhancing the chemotherapeutic treatment of tumor cells in a mammal with an antineoplastic alkylating agent, which causes cytotoxic lesions at the O 6 -position of guanine, by administering to a mammal an effective amount of one of the aforesaid compounds, 2,4-diamino-6-benzyloxy-s-triazine, 5-substituted 2,4-diamino-6-benzyloxypyrimidines, or 8-aza-O 6 -benzylguanine, and administering to the mammal an effective amount of an antineoplastic alkylating agent which causes cytotoxic lesions at the Deposition of guanine.

  本发明提供了AGT失活化合物，例如公式17-或9-取代的8-aza-O6-苄基鸟嘌呤、7,8-二取代的O6-苄基鸟嘌呤、7,9-二取代的O6-苄基鸟嘌呤、4（6）-取代的2-氨基-5-硝基-6（4）-苄氧嘧啶和4（6）-取代的2-氨基-5-亚硝基-6（4）-苄氧嘧啶，以及包含这些化合物和药用载体的制药组合物。本发明还提供了一种增强抗肿瘤烷化剂治疗哺乳动物肿瘤细胞的方法，该方法通过向哺乳动物投与上述化合物、2,4-二氨基-6-苄氧基-s-三嗪、5-取代的2,4-二氨基-6-苄氧基嘧啶或8-aza-O6-苄基鸟嘌呤的有效量，并向哺乳动物投与一种在鸟嘌呤O6位引起细胞毒性损伤的抗肿瘤烷化剂的有效量。
• Substituted O6-benzylguanines and 6(4)-benzyloxypyrimidines
  申请人：THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, Department of Health and Human Services

  公开号：EP1142893A1

  公开（公告）日：2001-10-10

  The present invention provides AGT inactivating compounds such as substituted O6-benzylguanines, 7- or 9-substituted 8-aza-O6-benzylguanines, 7,8-disubstituted O6-benzylguanines, 7,9-disubstituted O6-benzylguanines, 4(6)-substituted 2-amino-5-nitro-6(4)-benzyloxypyrimidines, and 4(6)-substituted 2-amino-5-nitroso-6(4)-benzyloxypyrimidines, as well as pharmaceutical compositions comprising such compounds along with a pharmaceutically acceptable carrier. The present invention further provides a method of enhancing the chemotherapeutic treatment of tumor cells in a mammal with an antineoplastic alkylating agent which causes cytotoxic lesion at the O6-position of guanine, by administering to a mammal an effective amount of one of the aforesaid compounds, 2,4-diamino-6-benzyloxy-s-triazine, 5-substituted 2,4-diamino-6-benzyloxypyrimidines, or 8-aza-O6-benzylguanine, and administering to the mammal an effective amount of an antineoplastic alkylating agent which causes cytotoxic lesions of the O6-postion of guanine.

  本发明提供 AGT 失活化合物，如取代的 O6-苄基鸟嘌呤、7-或 9-取代的 8-氮杂-O6-苄基鸟嘌呤、7,8-二取代的 O6-苄基鸟嘌呤、7,9-二取代的 O6-苄基鸟嘌呤、4(6)-取代的 2-氨基-5-亚硝基-6(4)-苄氧基嘧啶，和 4(6)-取代的 2-氨基-5-亚硝基-6(4)-苄氧基嘧啶，以及包含这些化合物和药学上可接受的载体的药物组合物。本发明进一步提供了一种方法，通过向哺乳动物施用有效量的上述化合物之一，用能在鸟嘌呤的 O6 位引起细胞毒性病变的抗肿瘤烷化剂加强对哺乳动物体内肿瘤细胞的化疗、2,4-二氨基-6-苄氧基-s-三嗪、5-取代的 2,4-二氨基-6-苄氧基嘧啶或 8-氮杂-O6-苄基鸟嘌呤，并向哺乳动物施用有效量的抗肿瘤烷化剂，使鸟嘌呤的 O6 位发生细胞毒性病变。
• Substituted 06- benzylguanines and 7- or 9- substituted 8-aza-06-benzylguanines
  申请人：THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, Department of Health and Human Services

  公开号：EP1518854A1

  公开（公告）日：2005-03-30

  The present invention provides AGT inactivating compounds such as 7- or 9-substituted 8- aza- O6-benzylguanines of formula (III) or (IV), and related substituted O6-benzyl guanines, as well as pharmaceutical compositions comprising such compounds along with a pharmaceutically acceptable carrier. The present invention further provides a method of enhancing the chemotherapeutic treatment of tumour cells in a mammal with an antineoplastic alkylating agent which causes cytotoxic lesions at the O6- position of guanine, by administering to a mammal an effective amount of one of the aforesaid compounds, 2,4-diamino-6-benzyloxy-s-triazine, or 8-aza-O6-benzylguanine, and administering to the mammal an effective amount of an antineoplastic alkylating agent which causes cytotoxic lesions at the O6- position of guanine.

  本发明提供了AGT失活化合物，如式(III)或(IV)的7-或9-取代的8-氮杂O6-苄基鸟嘌呤和相关的取代的O6-苄基鸟嘌呤，以及包含此类化合物和药学上可接受的载体的药物组合物。本发明进一步提供了一种用抗肿瘤烷化剂加强对哺乳动物体内肿瘤细胞的化疗治疗的方法，该抗肿瘤烷化剂可在鸟嘌呤的 O6-位上引起细胞毒性病变、向哺乳动物施用有效量的上述化合物之一、2,4-二氨基-6-苄氧基-s-三嗪或 8-氮杂-O6-苄基鸟嘌呤，并向哺乳动物施用有效量的抗肿瘤烷化剂，这种抗肿瘤烷化剂可在鸟嘌呤的 O6-位上引起细胞毒性病变。
• SUBSTITUTED O6 -BENZYLGUANINES AND 6(4)-BENZYLOXYPYRIMIDINES
  申请人：THE UNITED STATES OF AMERICA, as represented by the Secretary of the Department of Health and Human Services

  公开号：EP0775142A1

  公开（公告）日：1997-05-28