4-amino-1-((2,2-bis(hydroxymethyl)cyclopropylidene)methyl)pyrimidin-2(1H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-amino-1-((2,2-bis(hydroxymethyl)cyclopropylidene)methyl)pyrimidin-2(1H)-one
• 英文别名: 4-Amino-1-[[2,2-bis(hydroxymethyl)cyclopropylidene]methyl]pyrimidin-2-one
• 化学式: C₁₀H₁₃N₃O₃
• 分子量: 223.232
• InChiKey: KNRZCGSGZCQNMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  99.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-amino-1-((2,2-bis(hydroxymethyl)cyclopropylidene)methyl)pyrimidin-2(1H)-one 在 氨 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 19.0h， 生成 (Z)-4-amino-1-((2,2-bis(hydroxymethyl)cyclopropylidene)methyl)pyrimidin-2(1H)-one
  参考文献：
  名称：

  WO2019172835A5

  摘要：

  公开号：

  WO2019172835A5
• 作为产物：
  描述：

  2,2-bis(acetoxymethyl)methylenecyclopropane 在 溴 、 potassium carbonate 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 4-amino-1-((2,2-bis(hydroxymethyl)cyclopropylidene)methyl)pyrimidin-2(1H)-one
  参考文献：
  名称：

  WO2019172835A5

  摘要：

  公开号：

  WO2019172835A5

文献信息

• 2,2-bis-(hydroxymethyl)cyclopropylidenemethyl-purines and pyrmindines as antiviral agents
  申请人：Zemlicka Jiri

  公开号：US20050113393A1

  公开（公告）日：2005-05-26

  Compounds which are active against viruses have the following formulas: wherein B is a purine or pyrimidine heterocyclic ring or base. In a preferred embodiment, the purine include 6-aminopurine (adenine), 6-hydroxypurine (hypoxanthine), 2-amino-6-hydroxypurine (guanine), 2,6-diamino-purine, 2-amino-6-azidopurine, 2-amino-6-halo substituted purines such as 2-amino-6-chloropurine, 2-amino-6-fluoropurine, 2-amino-6-alkoxypurines such as 2-amino-6-methoxypurine, 2-amino-6-cyclopropylaminopurine, 2-amino-6-alkylamino or 2-amino-6-dialkylamino substituted purines, 2-amino-6-thiopurine, 2-amino-6-alkylthio substituted purines, 3-deazapurines, 7-deazapurines and 8-azapurines. The pyrimidine incorporates cytosine, uracil and thymine, 5-halo substituted cytosines and uracils, 5-alkyl substituted cytosines and uracils including derivatives with a saturated or unsaturated alkyl group and 6-azapyrimidines.

  具有抗病毒活性的化合物具有以下公式：其中B是嘌呤或嘧啶杂环环或碱基。在一个首选实施例中，嘌呤包括6-氨基嘌呤（腺嘌呤）、6-羟基嘌呤（次黄嘌呤）、2-氨基-6-羟基嘌呤（鸟嘌呤）、2,6-二氨基嘌呤，2-氨基-6-叠氮基嘌呤，2-氨基-6-卤代嘌呤，例如2-氨基-6-氯嘌呤，2-氨基-6-氟嘌呤，2-氨基-6-烷氧基嘌呤，例如2-氨基-6-甲氧基嘌呤，2-氨基-6-环丙基氨基嘌呤，2-氨基-6-烷基氨基或2-氨基-6-二烷基氨基嘌呤，2-氨基-6-硫嘌呤，2-氨基-6-烷硫代嘌呤，3-脱氮嘌呤，7-脱氮嘌呤和8-氮嘌呤。嘧啶包括胞嘧啶、尿嘧啶和胸腺嘧啶，5-卤代胞嘧啶和尿嘧啶，5-烷基代胞嘧啶和尿嘧啶，包括具有饱和或不饱和烷基基团的衍生物和6-氮杂嘧啶。
• 2,2-Bis-(hydroxymethyl)cyclopropylidenemethyl-Purines and -Pyrimidines As Antiviral Agents
  申请人：Zemlicka Jiri

  公开号：US20090118308A1

  公开（公告）日：2009-05-07

  Compounds which are active against viruses have the following formulas: wherein B is a purine or pyrimidine heterocyclic ring or base. In a preferred embodiment, the purine include 6-aminopurine (adenine), 6-hydroxypurine (hypoxanthine), 2-amino-6-hydroxypurine (guanine), 2,6-diamino-purine, 2-amino-6-azidopurine, 2-amino-6-halo substituted purines such as 2-amino-6-chloropurine, 2-amino-6-fluoropurine, 2-amino-6-alkoxypurines such as 2-amino-6-methoxypurine, 2-amino-6-cyclopropylaminopurine, 2-amino-6-alkylamino or 2-amino-6-dialkylamino substituted purines, 2-amino-6-thiopurine, 2-amino-6-alkylthio substituted purines, 3-deazapurines, 7-deazapurines and 8-azapurines. The pyrimidine incorporates cytosine, uracil and thymine, 5-halo substituted cytosines and uracils, 5-alkyl substituted cytosines and uracils including derivatives with a saturated or unsaturated alkyl group and 6-azapyrimidines.

  对病毒具有活性的化合物具有以下公式：其中B是嘌呤或嘧啶杂环环或碱基。在优选实施例中，嘌呤包括6-氨基嘌呤（腺嘌呤），6-羟基嘌呤（次黄嘌呤），2-氨基-6-羟基嘌呤（鸟嘌呤），2,6-二氨基嘌呤，2-氨基-6-叠氮基嘌呤，2-氨基-6-卤代嘌呤，例如2-氨基-6-氯嘌呤，2-氨基-6-氟嘌呤，2-氨基-6-烷氧基嘌呤，例如2-氨基-6-甲氧基嘌呤，2-氨基-6-环丙基氨基嘌呤，2-氨基-6-烷基氨基或2-氨基-6-二烷基氨基取代的嘌呤，2-氨基-6-硫代嘌呤，2-氨基-6-烷基硫代取代嘌呤，3-去氮嘌呤，7-去氮嘌呤和8-氮杂嘧啶。嘧啶包括胞嘧啶，尿嘧啶和胸腺嘧啶，5-卤代胞嘧啶和尿嘧啶，5-烷基取代的胞嘧啶和尿嘧啶，包括具有饱和或不饱和烷基的衍生物和6-氮杂嘧啶。
• 2,2-BIS-(HYDROXYMETHYL)CYCLOPROPYLIDENEMETHYL-PURINES AND -PYRIMIDINES AS ANTIVIRAL AGENTS
  申请人：Zemlicka Jiri

  公开号：US20110275652A1

  公开（公告）日：2011-11-10

  Compounds which are active against viruses have the following formulas: wherein B is a purine or pyrimidine heterocyclic ring or base. In a preferred embodiment, the purine include 6-aminopurine (adenine), 6-hydroxypurine (hypoxanthine), 2-amino-6-hydroxypurine (guanine), 2,6-diamino-purine, 2-amino-6-azidopurine, 2-amino-6-halo substituted purines such as 2-amino-6-chloropurine, 2-amino-6-fluoropurine, 2-amino-6-alkoxypurines such as 2-amino-6-methoxypurine, 2-amino-6-cyclopropylaminopurine, 2-amino-6-alkylamino or 2-amino-6-dialkylamino substituted purines, 2-amino-6-thiopurine, 2-amino-6-alkylthio substituted purines, 3-deazapurines, 7-deazapurines and 8-azapurines. The pyrimidine incorporates cytosine, uracil and thymine, 5-halo substituted cytosines and uracils, 5-alkyl substituted cytosines and uracils including derivatives with a saturated or unsaturated alkyl group and 6-azapyrimidines.

  具有抗病毒活性的化合物具有以下公式：其中B是一种嘌呤或嘧啶杂环环或碱基。在优选实施例中，嘌呤包括6-氨基嘌呤（腺嘌呤）、6-羟基嘌呤（次黄嘌呤）、2-氨基-6-羟基嘌呤（鸟嘌呤）、2,6-二氨基嘌呤、2-氨基-6-叠氮基嘌呤、2-氨基-6-卤代嘌呤，例如2-氨基-6-氯嘌呤、2-氨基-6-氟嘌呤、2-氨基-6-烷氧基嘌呤，例如2-氨基-6-甲氧基嘌呤、2-氨基-6-环丙胺基嘌呤、2-氨基-6-烷基氨基或2-氨基-6-二烷基氨基取代的嘌呤，2-氨基-6-硫代嘌呤，2-氨基-6-烷基硫代取代的嘌呤，3-脱氮嘌呤，7-脱氮嘌呤和8-氮杂嘧啶。嘧啶包括胞嘧啶、尿嘧啶和胸腺嘧啶，5-卤代胞嘧啶和尿嘧啶，5-烷基取代的胞嘧啶和尿嘧啶，包括具有饱和或不饱和烷基的衍生物和6-氮杂嘧啶。
• 2,2-BIS(HYDROXYMETHYL)CYCLOPROPYLIDENEMETHYL - PURINES AND -PYRIMIDINES AS ANTIVIRAL AGENTS
  申请人：WAYNE STATE UNIVERSITY

  公开号：EP1490368B1

  公开（公告）日：2011-08-03
• CANCER TREATMENT WITH (2,2-BISHYDROXYMETHYL) METHYLENECYCLOPROPANE NUCLEOTIDES
  申请人：MEDIVIR AB

  公开号：US20200399295A1

  公开（公告）日：2020-12-24

  The invention provides a compound of formula (I) wherein B is a nucleobase; U is O or S; R x is —OC(═O)R y , —OC(═O)CH(R y )NH 2 , —OCH 2 OC(═O)R y ; R y is optionally substituted alkyl or alkenyl or the side chain of a natural or unnatural amino acid R 1 is H, or optionally substituted phenyl, benzyl, naphthyl, pyridyl or indolyl, or R x and R 1 together define a bond thus forming a cyclic phosphate; R 2 and R 2′ together define the side chain of a natural or unnatural amino acid; R 3 is optionally substituted alkyl, cycloalkyl, phenyl or benzyl; and pharmaceutically acceptable salts and compositions thereof which are useful in the treatment of cancer, especially leukemias.