4,6-dihydroxy-2,8-dimercapto-5-(p-nitrophenyl)-5H-pyrano[2,3-d:6,5-d']dipyrimidine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,6-dihydroxy-2,8-dimercapto-5-(p-nitrophenyl)-5H-pyrano[2,3-d:6,5-d']dipyrimidine
• 英文别名: 9-(4-nitrophenyl)-5,13-bis(sulfanyl)-2-oxa-4,6,12,14-tetrazatricyclo[8.4.0.03,8]tetradeca-1(14),3,5,7,10,12-hexaene-7,11-diol
• 化学式: C₁₅H₉N₅O₅S₂
• 分子量: 403.399
• InChiKey: UYLYXNZSRMQYRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  202
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  碘乙酸 、 4,6-dihydroxy-2,8-dimercapto-5-(p-nitrophenyl)-5H-pyrano[2,3-d:6,5-d']dipyrimidine 在 sodium hydroxide 作用下， 以86%的产率得到[(5-(4-nitrophenyl)-4,6-dioxo-3,5,6,7-tetrahydro-4H-pyrano[2,3-d:6,5-d']dipyrimidine-2,8-diyl)di(sulfanyl)]diacetic acid
  参考文献：
  名称：

  Azoles and Azines: CXIX. Alkylation of 5,5'-(4-Nitrobenzylidene)bis(2-thiobarbituric) Acid and 5-(4-Nitrophenyl)-2,8-dithioxo-5,7,8,9-tetrahydro-2H-pyrano[2,3-d:6,5-d']dipyrimidine-4,6(1H,3H)-dione with Haloacetic Acids and Their Esters

  摘要：

  5,5'-(4-Nitrobenzylidene)bis(2-thiobarbituric) acid and 5-(4-nitrophenyl)-2,8-dithioxo-5,7,8,9-tetrahydro-2H-pyrano[2,3-d:6,5-d']dipyrimidine-4,6(1H,3H)-dione, similar to unsubstituted 2-thiobarbituric acid, readily react with haloacetic acids and their esters to form regioselectively the S-alkylation products. The alternative routes to 5,5'-(4-nitrobenzylidene)bis[(4-hydroxy-6-oxo-1,6-dihydropyrimidine-5,2-diyl)-sulfanyl]diacetic acids, based on condensation of 4,6-dihydroxypyrimidin-2-ylthioacetic acid with carbonyl compounds followed by cyclodehydration to [(5-(4-nitrophenyl)-4,6-dioxo-3,5,6,7-tetrahydro-4H-pyrano[2,3-d:6,5-d']dipyrimidine-2,8-diyl)di(sulfanyl)]diacetic acid derivatives, are less efficient. Alkylation of 2-thiobarbituric acid with ethyl bromoacetate in ethanol in the presence of alkali yields 5-(2-oxo-2,5-dihydro-l,3-thiazol-4-yl)-2-thiobarbituric acid.

  DOI：

  10.1023/b:rugc.0000025180.58032.54
• 作为产物：
  描述：

  5,5'-(4-nitrophenylmethylene)bis(2-thiobarbituric acid), pyridinium salt 在 phosphorus pentoxide 、 三氯氧磷 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以85%的产率得到4,6-dihydroxy-2,8-dimercapto-5-(p-nitrophenyl)-5H-pyrano[2,3-d:6,5-d']dipyrimidine
  参考文献：
  名称：

  5H-Pyrano[2,3-d: 6,5-d']dipyrimidine derivatives having an antibacterial, antiviral and immuno-modulating activity

  摘要：

  本发明涉及具有以下结构式的新化合物，该化合物具有抗菌、抗病毒和免疫调节活性。

  公开号：

  US06340755B1

文献信息

• One-pot Synthesis of Novel 2,8-dithioxopyrano[2,3-d:6,5-d′]dipyrimidine-4,6(1<i>H</i>)-dione Catalyzed by<i>p</i>-Toluenesulfonic Acid
  作者：N. O. Mahmoodi、B. Sharifzadeh、M. Mamaghani、K. Tabatabaeian、S. Shoja

  DOI：10.1002/jhet.2165

  日期：2016.9

  synthesized by a clean and efficient methodologies involving one‐pot regioselective and chemoselective reactions between two moles substituted thiobarbituric acid and 1 mol various aromatic aldehydes in the presence of p‐toluenesulfonic acid as a catalyst in EtOH with good yields in compression with alternative conditions such as microwave and promoted ultrasound. All of the compounds have been characterized

  通过一种干净有效的方法，涉及两个之间的一锅区域选择性和化学选择性反应，合成了新型2,8-二硫代吡喃并[2,3-d：6,5-d']双嘧啶-4,6（1 H）-二酮衍生物在对甲苯磺酸作为乙醇中的催化剂存在下，可使用50摩尔/摩尔的取代的硫代巴比妥酸和1摩尔的各种芳族醛，在微波和超声等替代条件下，压缩后的收率很高。所有化合物均已通过IR，1 H NMR，13 C NMR光谱数据和元素分析进行了表征。
• 5H-Pyrano&lsqb;2,3-d: 6,5-d'&rsqb;dipyrimidine derivatives having an antibacterial, antiviral and immuno-modulating activity
  申请人：Natural Drug Sciences LLC

  公开号：US06340755B1

  公开（公告）日：2002-01-22

  The present invention relates to novel compounds having the formula The compounds have antibacterial, antiviral, and immuno-modulating activity.

  本发明涉及具有以下结构式的新化合物，该化合物具有抗菌、抗病毒和免疫调节活性。
• Moskvin; Polkovnikova; Ivin, Russian Journal of General Chemistry, 1998, vol. 68, # 8, p. 1300 - 1305
  作者：Moskvin、Polkovnikova、Ivin

  DOI：——

  日期：——
• EP1669357
  申请人：——

  公开号：——

  公开（公告）日：——
• Substance which exhibits antiviral and antibacterial activity and is based on derivatives of 2,8-dithioxo-1h-pyrano[2,3d 6,5-d']dipyrimidyne and 10-aza-analogue thereof
  申请人：Tets Veniaminovich Viktor

  公开号：US20070037838A1

  公开（公告）日：2007-02-15

  The invention relates to organic chemistry and medicine, more specifically to synthetic pyrimidine derivatives, i.e. 2,8-dithioxo-1H-pyrano[2,3d,6,5-d′]dipyrimidyne and 10-aza-analogue thereof and to the complexes and salts thereof which exhibit antiviral and antimicrobial activity. Said invention can be used for medicine and veterinary science for treating viral diseases, bacteria-induced diseases and for cosmetology in the form of an additive for preventing and treating infections. The aim of said invention is to develop a novel more efficient substance exhibiting antiviral and antimicrobial activity. The inventive substance which exhibits antiviral and antimicrobial activity is based on derivatives of 2,8-dithioxo-1H-pyrano[2,3d,6,5-d′]dipyrimidyne and 10-aza-analogue thereof and characterised in that it comprises the derivative of said group of general formula A1, M, wherein X is selected from a group O, NH, N-Alkyl; R1 is selected from a group H, Oh, Cl, O-Alkyl, NH 2 , NH-Alkyl, NH—Ar, N(Alkyl) 2 , SH, S-Alkyl, S—Ar, S-Hetaryl; R 2 is selected from a group C 6 H 5 , Aryl, R3 is selected from a group H, Cl, O-Alkyl, NH 2 , NH-Alkyl, NH—Ar, S-Heratyl, M is absent or selected from a group of Na, K, Li, ammonium cation or another pharmacologically acceptable cation; or said complex of pharmacologically acceptable cation with the anion of one of derivatives Al (above-mentioned variants R 1 —R 3 ).