6-benzamido-9-(chloromercuri)purine | 94979-83-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 6-benzamido-9-(chloromercuri)purine
• 英文别名: 9-Chlormercuri-6-benzamidopurin；Chloro[N-(9H-purin-6-yl)benzamidato]mercury；mercury(2+);N-(7H-purin-6-yl)benzenecarboximidate;chloride
• CAS: 94979-83-6
• 化学式: C₁₂H₈N₅O*Cl*Hg
• 分子量: 474.271
• InChiKey: FRARYBUCDQOCGN-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-benzamido-9-(chloromercuri)purine 生成 9-(6-deoxy-α-L-talopyranosyl)adenine
  参考文献：
  名称：

  LERNER, L. M.;SHOID, B.;GAETJENS, E., J. MED. CHEM., 30,(1987) N 8, 1521-1525

  摘要：

  DOI：

文献信息

• An asymmetric approach to 2-deoxynucleosides via organosulfur building blocks as chemical chameleons
  作者：Barry M. Trost、Christoph Nübling

  DOI：10.1016/0008-6215(90)84067-5

  日期：1990.7

  asymmetric synthesis of 6-N-benzoyl-5'-O-benzyl-2'-deoxyadenosine and its a anomer from non-carbohydrate building blocks is achieved in 7 steps. The sequence builds the basic structures using bis(methylthio)methane and methylthiomethyl phenyl sulfone as both nucleophilic and electrophilic building blocks, a feature that suggests their behavior as chemical chameleons. The asymmetric induction is achieved

  由非碳水化合物结构单元实现6-N-苯甲酰基-5'-O-苄基-2'-脱氧腺苷及其异构体的不对称合成可通过7个步骤完成。该序列使用双（甲硫基）甲烷和甲硫基甲基苯基砜作为亲核和亲电构件来构建基本结构，这一特征表明它们作为化学变色龙的行为。利用基于催化不对称环氧化的动力学拆分来实现不对称诱导。
• Homonucleoside phosphonic acid-I
  作者：Hans P. Albrecht、Gordon H. Jones、John G. Moffatt

  DOI：10.1016/0040-4020(84)85105-4

  日期：1984.1

  β-D-ribofuranose 13, This compound, or the related glycosyl chloride, was condensed with several purine and pyrimidine bases and all protecting groups were removed by mild alkaline treatment via a series of intramolecular cyclizations and hydrolysis. In this manner the phosphonate analogs of nucleoside 3'-phosphates derived from adenine, 6-dimethylaminopurine, uracil, thymine, and cytosine were prepared

  描述了3'-脱氧-3'-二羟基次膦酰基甲基核糖核苷3（核苷3'-磷酸的等排磷酸酯类似物）的一般合成路线。这涉及用亚甲基二膦酸四乙酯6烷基化1,2; 5,6-二-O-异亚丙基-α-D-核糖-六呋喃糖-3-ulose 7），然后进行立体选择性催化还原并裂解C 6生成3-脱氧-3-二乙氧基次膦基甲基-1，2-O-异亚丙基-α- D12a。苯甲酰化，然后进行乙酰分解，然后生成关键的结晶中间体1,2-二-O-乙酰基-5-O-苯甲酰基-3-脱氧-3-二乙氧基次膦基甲基-β-D-呋喃呋喃糖13将该化合物或相关的糖基氯与几个嘌呤和嘧啶碱基缩合，并通过一系列分子内环化和水解，通过温和的碱处理除去所有保护基。以这种方式制备了衍生自腺嘌呤，6-二甲基氨基嘌呤，尿嘧啶，胸腺嘧啶和胞嘧啶的核苷3'-磷酸的膦酸酯类似物。
• Synthesis of Cyclic α-Amino Acids. IV. Syntheses of Adenine Nucleosides of 3-Amino-3-<i>C</i>-carboxy-3-deoxy-D-ribofuranose and 3-Amino-3-<i>C</i>-carboxy-3-deoxy-D-ribopyranose
  作者：Hiroaki Yanagisawa、Mitsuhiro Kinoshita、Saburo Nakada、Sumio Umezawa

  DOI：10.1246/bcsj.43.246

  日期：1970.1

  β-D-ribofuranosyl)adenine (I) and 9-(3′-amino-3′-C-carboxy-3′-deoxy-β-D-ribopyranosyl)adenine (II) have been synthesized. They are the first examples of nucleoside-derivatives which have an α-amino acid structure in their furanose or pyranose ring. A masked derivative (VII) of α-D-erythro-pentofuranos-3-ulose was converted into a hydantoin derivative (IX), which was acetolyzed and then treated with

  9-(3'-Amino-3'-C-carboxy-3'-deoxy-β-D-ribofuranosyl)adenine (I) 和 9-(3'-amino-3'-C-carboxy-3'-deoxy -β-D-吡喃核糖基）腺嘌呤（II）已被合成。它们是在其呋喃糖或吡喃糖环中具有α-氨基酸结构的核苷衍生物的第一个例子。α-D-赤型-pentofuranos-3-ulose 的掩蔽衍生物 (VII) 转化为乙内酰脲衍生物 (IX)，将其乙酰水解，然后用无水氯化氢处理，得到酰基糖基氯 (XI)。该衍生物与氯汞-6-苯甲酰氨基嘌呤缩合，然后水解得到 I。用甲醇氯化氢处理乙内酰脲衍生物 (IX)，然后水解得到甲基 3-氨基-3-C-羧基-3-脱氧-α-D -核糖苷（XVII），已发现其与先前报道的甲基 3-氨基-3-C-羧基-3-脱氧-α-D-吡喃戊糖苷的异构体之一相同。该酸乙酯的 1-O-乙酰基-3-N-苯甲酰基-2
• Preparation and antileukemic screening of some new 6'-deoxyhexopyranosyladenine nucleosides
  作者：Leon M. Lerner、Bertrum Sheid、Eric Gaetjens

  DOI：10.1021/jm00391a044

  日期：1987.8

  for activity. The new nucleosides were 9-(6-deoxy-beta-D-glucopyranosyl)adenine (2), 9-(6-deoxy-beta-D-allopyranosyl)adenine (3), 9-(6-deoxy-alpha-L-talopyranosyl)adenine (4), 9-alpha-D-rhamnopyranosyladenine (5), and 9-(6-deoxy-alpha-L-idopyranosyl)adenine (6). In addition, 9-(6-deoxy-alpha-L-sorbofuranosyl)adenine (7) was isolated from the same preparation as 6. None of the new nucleosides 2-7 had

  9-β-D-富勒索糖基腺嘌呤（1）对培养物中生长的L1210细胞的抗白血病活性较弱。通过标准程序合成了几种新的6'-脱氧己吡喃糖基腺嘌呤核苷，并对其活性进行了测定。新的核苷是9-（6-脱氧-β-D-吡喃葡萄糖基）腺嘌呤（2），9-（6-脱氧-β-D-戊吡喃糖基）腺嘌呤（3），9-（6-脱氧-α-L -talopyranosyl）腺嘌呤（4），9-α-D-鼠李糖吡喃糖基腺嘌呤（5）和9-（6-脱氧-α-L-idopyranosyl）腺嘌呤（6）。另外，从与6相同的制剂中分离出9-（6-脱氧-α-L-山梨糖醛酸基）腺嘌呤（7）。新的核苷2-7都没有抗培养中的L1210细胞的活性。还测试了许多与结构相关的其他已知核苷的活性。其中一种9-α-L-阿拉伯吡喃型腺嘌呤腺苷具有活性，但明显弱于1。
• Preparation of the .alpha. and .beta. anomers of 9-(3,5-dideoxy-D-glycero-pent-4-enofuranosyl)adenine and their activity with leukemia L1210 cells in vitro
  作者：Leon M. Lerner

  DOI：10.1021/jm00349a011

  日期：1982.7

  correct. A new synthesis of 5 is described. 3,5-Dideoxy-5-iodo-1,2-O-isopropylidene-alpha-D-erythro-pentofuranose (1) and 3,5-dideoxy-5-iodo-1,2-O-isopropylidene-beta-L-threo-pentofuranose (6) were prepared as starting materials. The isopropylidene groups were exchanged for acetyl groups by acetolysis, and the resulting diacetates (2 and 7) were isopropylidene groups were coupled with 6-(benzamidochloromercuri)purine

  先前报道的9-（3,5-二脱氧-β-D-甘油-戊-4-enofuranosyl）腺嘌呤的制备方法（5）不正确。描述了5的新合成。3,5-二甲氧基-5-碘-1,2-O-异亚丙基-α-D-赤-戊呋喃糖（1）和3,5-二甲氧基-5-碘-碘-1,2-O-异亚丙基-β-L制备了苏式-戊-戊呋喃糖（6）作为起始原料。通过乙酰分解将异亚丙基交换为乙酰基，并且通过四氯化钛方法将所得的二乙酸酯（2和7）与异亚丙基与6-（苯甲酰氨基氯汞）嘌呤偶联。通过色谱法将被保护的核苷（3和8）与未反应的糖分离，并用1，8-二氮杂双环-[5.4.0] undec-7-烯处理，然后除去保护基团。9-（3,5-dideoxy-D-glycerpent-pent-4-enofuranosyl）Adenine（4 and 5，的α和β端基异构体 分别以3：1的比例从3中获得。7与碱的缩合以更高的收率得到β-核苷5。未检测到4。当在

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