2-<<(N,N-Dimethylamino)methylene>amino>-4(3H)-oxo-3-<(pivaloyloxy)methyl>-5H-pyrrolo<3,2-d>pyrimidine | 151587-58-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 2-<<(N,N-Dimethylamino)methylene>amino>-4(3H)-oxo-3-<(pivaloyloxy)methyl>-5H-pyrrolo<3,2-d>pyrimidine
• 英文别名: 2-{[(dimethylamino)methylidene]amino}-3,5-dihydro-3-[(pivaloyloxy)methyl]-4H-pyrrolo[3,2-d]pyrimidin-4-one；[2-(dimethylaminomethylideneamino)-4-oxo-5H-pyrrolo[3,2-d]pyrimidin-3-yl]methyl 2,2-dimethylpropanoate
• CAS: 151587-58-5
• 化学式: C₁₅H₂₁N₅O₃
• 分子量: 319.363
• InChiKey: TXSDMMQNNZXCGH-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于二氯甲烷、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  90.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-<<(N,N-Dimethylamino)methylene>amino>-4(3H)-oxo-3-<(pivaloyloxy)methyl>-5H-pyrrolo<3,2-d>pyrimidine 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以96%的产率得到2-氨基-3,5-二氢吡咯并[3,2-D]嘧啶-4-酮
  参考文献：
  名称：

  9-去氮鸟嘌呤合成工艺的改进方法

  摘要：

  本发明公开了一种9‑去氮鸟嘌呤合成工艺的改进方法，克服了现有9‑去氮鸟嘌呤合成工艺中存在的产率低、成本高等缺点，本发明方法对9‑去氮鸟嘌呤制备方法中脱除保护基关键步骤进行改进，将含保护基团的9‑去氮鸟嘌呤溶于有机溶剂中，加入适量的肼或者胺，加热下反应1‑24小时，减压蒸馏除去有机溶剂，再通过抽滤及有机溶剂和水洗涤得到9‑去氮鸟嘌呤。本申请中9‑去氮鸟嘌呤可应用于设计嘌呤核苷磷酸化酶抑制剂，在抗肿瘤、抗艾滋病毒各种疾病新药研发筛选中有重要的应用，本发明提供的脱保护基方法具有操作简单、高效、原料成本低、收率高等优点，在具体生产中非常实用。

  公开号：

  CN110590786B
• 作为产物：
  描述：

  2-氨基-6-甲基-5-硝基-3H-嘧啶-4-酮 在 sodium dithionite 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 2-<<(N,N-Dimethylamino)methylene>amino>-4(3H)-oxo-3-<(pivaloyloxy)methyl>-5H-pyrrolo<3,2-d>pyrimidine
  参考文献：
  名称：

  Pyrrolo[3,2-d]pyrimidine Folate Analogs: "Inverted" Analogs of the Cytotoxic Agent LY231514

  摘要：

  N-{4-[2-(2-Amino-4(3H)-oxo-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid (3a) and N-{4-[3-(2-amino-4(3H)-oxo-5h-pyrrolo[3,2-d]pyrimidin-5-yl)propyl]benzoyl}-L-glutamic acid (3b) were synthesized as potential anticancer agents.

  DOI：

  10.1021/jo00129a040

文献信息

• Process for preparing 2-pyrrolidinyl-1H-pyrrolo&lsqb;3,2-d&rsqb;pyrimidine inhibitors of nucleoside metabolism
  申请人：Industrial Research Limited

  公开号：US06693193B1

  公开（公告）日：2004-02-17

  A process of preparing a compound of the formula (I) wherein B is chosen from OH, NH2, NHR, H or halogen; D is chosen from OH, NH2, NHR, H halogen or SCH3; R is an optionally substituted alkyl, aralkyl or aryl group; and Z is selected from OH, hydrogen, halogen, hydroxy, SQ or OQ, Q is an optionally substituted all, aralkyl or aryl group; or a tautomer thereof; or a pharmaceutically acceptable salt thereof; or an ester thereof; or a prodrug thereof, which comprises reacting a compound of the formula (II)  with an anion produced by abstraction of the bromine or iodine atom from a compound of formula (XIX),  to form a compound of formula (XX) The compound of formula (XX) is N- and O-deprotected to obtain the compound of formula (I).

  将公式（I）的化合物制备过程翻译成中文： 其中B选择自OH、NH2、NHR、H或卤素；D选择自OH、NH2、NHR、H、卤素或SCH3；R是可选择取代的烷基、芳基烷基或芳基；Z选择自OH、氢、卤素、羟基、SQ或OQ，Q是可选择取代的烷基、芳基烷基或芳基；或其互变异构体；或其药学上可接受的盐；或其酯；或其前药，包括将公式（II）的化合物与通过从公式（XIX）的化合物中提取溴或碘原子而产生的负离子反应，形成公式（XX）的化合物。公式（XX）的化合物经N-和O去保护得到公式（I）的化合物。
• Synthesis of 9-Halogenated 9-DeazaguanineN7-(2?-Deoxyribonucleosides)
  作者：Frank Seela、Khalil?I. Shaikh、Thomas Wiglenda、Peter Leonard

  DOI：10.1002/hlca.200490224

  日期：2004.10

  The syntheses of N7-glycosylated 9-deazaguanine 1a as well as of its 9-bromo and 9-iodo derivatives 1b,c are described. The regioselective 9-halogenation with N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS) was accomplished at the protected nucleobase 4a (2-[(dimethylamino)methylidene]amino}-3,5-dihydro-3-[(pivaloyloxy)methyl]-4H-pyrrolo[3,2-d]pyrimidin-4-one). Nucleobase-anion glycosylation

  描述了N 7-糖基化的9-脱氮鸟嘌呤1a以及其9-溴和9-碘衍生物1b，c的合成。区域选择性9-卤化用Ñ溴代琥珀酰亚胺（NBS）和Ñ碘代丁二酰亚胺（NIS）的混合物在所述保护的核碱基完成4A [（二甲基氨基）亚甲基]氨基} -3,5-二氢-3 - - [（新戊酰氧基（2- ）甲基] -4 H-吡咯并[3,2- d ]嘧啶-4-一）。4a – c的碱基碱基阴离子糖基化与2-deoxy-3,5- di - O-（p -toluoyl）-α-D- erythro-戊呋喃糖基氯（5）提供了受完全保护的中间体6a – c（方案2）。将它们用0.01M NaOMe脱保护，得到糖去保护的衍生物8a – c（方案3）。在较高浓度（0.1M NaOMe）下，新戊酰氧基甲基基团也被除去，得到7a – c，同时浓。水 NH 3溶液提供了核苷1a – c。在D 2 O中，糖的构象总是偏向S（67-61％）。
• Structural-based design and synthesis of novel 9-deazaguanine derivatives having a phosphate mimic as multi-substrate analogue inhibitors for mammalian PNPs
  作者：Sadao Hikishima、Mariko Hashimoto、Lucyna Magnowska、Agnieszka Bzowska、Tsutomu Yokomatsu

  DOI：10.1016/j.bmc.2010.01.062

  日期：2010.3

  9-(5',5'-Difluoro-5'-phosphonopentyl)-9-deazaguanine (DFPP-DG) was designed as a multi-substrate analogue inhibitor against purine nucleoside phosphorylase (PNP) on the basis of X-ray crystallographic data obtained for a binary complex of 9-(5',5'-difluoro-5'-phosphonopentyl)guanine (DFPP-G) with calf-spleen PNP. DFPP-DG and its analogous compounds were synthesized by the Sonogashira coupling reaction between a 9-deaza-9-iodoguanine derivative and omega-alkynyldifluoromethylene phosphonates as a key reaction. The experimental details focused on the synthetic chemistry along with some insights into the physical and biological properties of newly synthesized DFPP-DG derivatives are disclosed. (C) 2010 Elsevier Ltd. All rights reserved.
• An expeditious synthesis of 2-amino-4(3)-oxo-5-pyrrolo[3,2-]pyrimidine (9-Deazaguanine)
  作者：Edward C. Taylor、Wendy B. Young、Cary C. Ward

  DOI：10.1016/s0040-4039(00)60633-0

  日期：1993.9

  9-Deazaguanine has been synthesized in five steps from 2-amino-6-methyl-5-nitro-4(3H)-pyrimidinone by a modification of the Batcho-Leimgruber indole synthesis.
• SYNTHESIS AND BASE PAIRING PROPERTIES OF 9-DEAZAPURINE N⁷-NUCLEOSIDES IN OLIGONUCLEOTIDE DUPLEXES AND TRIPLEXES
  作者：P. Leonard、T. Wiglenda、F. Seela

  DOI：10.1081/ncn-100002536

  日期：2001.3.31

  The 9-deazaguanine N-7-2'-deoxyribofuranoside (3) as well as the bromo and iodo derivatives 4a,b were synthesized and incorporated in oligonculeotide duplexes and triplexes. Their base pairing properties were investigated and compared with those of the parent purine N-7-2'-deoxyribofuanosides.