2,4-二甲氧基-5H-吡咯并[3,2-d]嘧啶 | 84538-40-9

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 中文名称: 2,4-二甲氧基-5H-吡咯并[3,2-d]嘧啶
• 中文别名: 2,4-二甲氧基-5H-吡咯并[3,2-D]嘧啶
• 英文名称: 2,4-dimethoxy-5H-pyrrolo<3,2-d>pyrimidine
• 英文别名: 2,4-dimethoxypyrrolo<3,2-d>pyrimidine；2,6-dimethoxy-9-deazapurine；2,4-dimethoxy-5H-pyrrolo[3,2-d]pyrimidine
• CAS: 84538-40-9
• 化学式: C₈H₉N₃O₂
• 分子量: 179.178
• InChiKey: GXIYYDQWNQWIBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  2,4-二甲氧基-5H-吡咯并[3,2-d]嘧啶 在 氢氧化钾 、 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 为溶剂， 生成 3-(2,4-Dimethoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-propane-1,2-diol
  参考文献：
  名称：

  Otmar, Miroslav; Masojidkova, Milena; Holy, Antonin, Collection of Czechoslovak Chemical Communications, 1996, vol. 61, p. S49 - S51

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-二氯-5-硝基-6-甲基嘧啶 在 T₁-Raney nickel 氢气 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.17h， 生成 2,4-二甲氧基-5H-吡咯并[3,2-d]嘧啶
  参考文献：
  名称：

  Synthetic strategies for 2,4-dimethoxypyrrolo[3,2-d]pyrimidine

  摘要：

  DOI：

  10.1021/jo00155a026

文献信息

• Condensed Heteroaromatic Ring Systems. XXI. Synthesis of Pyrrolo(2,3-d)pyrimidines and Pyrrolo(3,2-d)pyrimidines.
  作者：Takao SAKAMOTO、Chisato SATOH、Yoshinori KONDO、Hiroshi YAMANAKA

  DOI：10.1248/cpb.41.81

  日期：——

  Pyrrolo[2, 3-d]pyrimidines and pyrrolo[3, 2-d]pyrimidines were synthesized in high yields by the palladiumcatalyzed reaction of 4-acetylamino-5-bromopyrimidines and 5-acetylamino-4-iodopyrimidines with (Z)-1-ethoxy-2-(tributylstannyl)ethene followed by cyclization under acidic conditions.

  在钯催化下，4-乙酰氨基-5-溴嘧啶和 5-乙酰氨基-4-碘嘧啶与(Z)-1-乙氧基-2-(三丁基锡)乙烯反应，然后在酸性条件下环化，高产率合成了吡咯并[2,3-d]嘧啶和吡咯并[3,2-d]嘧啶。
• A novel method for the synthesis of 6,7-unsubstituted pyrrolo[3,2-]pyrimidines
  作者：Thomas L. Cupps、Dean S. Wise、Leroy B. Townsend

  DOI：10.1016/s0040-4039(00)85706-8

  日期：1982.1

  The synthesis of 2,4-dimethoxypyrrolo[3,2-d]pyrimidine (4) is described. This facile, 3-step synthesis involves the bromination of 2,4-dimethoxy-6-methyl-5-nitropyrimidine (1), and the subsequent conversion of compound 1 into compound 4.

  描述了2，4-二甲氧基吡咯并[3，2-d]嘧啶（4）的合成。这种简便的3步合成涉及2,4-二甲氧基-6-甲基-5-硝基嘧啶（1）的溴化反应，然后将化合物1转化为化合物4。
• [EN] PROCESS FOR PREPARING INHIBITORS OF NUCLEOSIDE METABOLISM<br/>[FR] PROCEDE PERMETTANT DE PREPARER DES INHIBITEURS DU METABOLISME DES NUCLEOSIDES
  申请人：IND RES LTD

  公开号：WO2000061783A2

  公开（公告）日：2000-10-19

  A process of preparing a compound of 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 alkyl, 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 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).

  制备式(I)化合物的过程，其中B从OH、NH2、NHR、H或卤素中选择；D从OH、NH2、NHR、H、卤素或SCH3中选择；R为可选取代的烷基、芳基烷基或芳基基团；Z从OH、氢、卤素、羟基、SQ或OQ中选择，Q为可选取代的烷基、芳基烷基或芳基基团；或其互变异构体；或其药物可接受盐；或其酯；或其前药。包括将式(II)化合物与从式(XIX)化合物中提取溴或碘原子所产生的阴离子反应，以形成式(XX)化合物。将式(XX)化合物进行N-和O-去保护即可获得式(I)化合物。
• Process for preparing inhibitors of nucleoside metabolism
  申请人：Furneaux Hubert Richard

  公开号：US20070161667A1

  公开（公告）日：2007-07-12

  A process of preparing a compound of the formula (I) wherein B is chosen from OH, NH 2 , NHR, H or halogen; D is chosen from OH, NH 2 , NHR, H halogen or SCH 3 ; 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 alkyl, 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),

  制备公式（I）化合物的过程，其中B选自OH，NH2，NHR，H或卤素；D选自OH，NH2，NHR，H，卤素或SCH3；R是可选取的取代基的烷基，芳基烷基或芳基；Z选自OH，氢，卤素，羟基，SQ或OQ，Q是可选取的取代基的烷基，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。该过程包括将公式（II）化合物与从公式（XIX）化合物中提取溴或碘原子所产生的阴离子反应。
• Novel halogenated 3-deazapurine, 7-deazapurine and alkylated 9-deazapurine derivatives of l-ascorbic or imino-l-ascorbic acid: Synthesis, antitumour and antiviral activity evaluations
  作者：Maja Stipković Babić、Damjan Makuc、Janez Plavec、Tamara Martinović、Sandra Kraljević Pavelić、Krešimir Pavelić、Robert Snoeck、Graciela Andrei、Dominique Schols、Karlo Wittine、Mladen Mintas

  DOI：10.1016/j.ejmech.2015.08.008

  日期：2015.9

  Keeping the potential synergy of biological activity of synthetic anomalous derivatives of deazapurines and L-ascorbic acid (L-AA) in mind, we have synthesized new 3-, 7- and 9-deazapurine derivatives of L-ascorbic (1-4, 8-10, 13-15) and imino-L-ascorbic acid (5-7, 11, 12, 16-19). These novel compounds were evaluated for their cytostatic and antiviral activity in vitro against a panel of human malignant tumour cell lines and normal murine fibroblasts (3T3). Among all evaluated compounds, the 9-deazapurine derivative of L-AA (13) exerted the most potent inhibitory activity on the growth of CEM/0 cells (IC50 = 4.1 +/- 1.8 mu M) and strong antiproliferative effect against L1210/0 (IC50 = 4.7 +/- 0.1 mu M) while the 9-deazahypoxanthine derivative of L-AA (15) showed the best effect against HeLa cells (IC50 = 5.6 +/- 1.3 mu M) and prominent effect on L1210/0 (IC50 = 4.5 +/- 0.5 mu M). Furthermore, the 9-deazapurine derivative disubstituted with two imino-L-AA moieties (18) showed the best activity against L1210/0 tumour cells (IC50 = 4.4 +/- 0.3 mu M) and the most pronounced antiproliferative effects against MiaPaCa-2 cells (IC50 = 5.7 +/- 0.2 mu M). All these compounds showed selective cytostatic effect on tumour cell lines in comparison with embryonal murine fibroblasts (3T3). When evaluating their antiviral activity, the 3-deazapurine derivative of L-AA (3) exhibited the highest activity against both laboratory-adapted strains of human cytomegalovirus (HCMV) (AD-169 and Davis) with EC50 values comparable to those of the well-known anti-HCMV drug ganciclovir and without cytotoxic effects on normal human embryonal lung (HEL) cells. (C) 2015 Elsevier Masson SAS. All rights reserved.

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