6-N-(benzoyl)-9-(ethoxycarbonylmethyl)adenine | 171406-46-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-N-(benzoyl)-9-(ethoxycarbonylmethyl)adenine
• 英文别名: N6-Benzoyl-9-ethoxycarbonylmethyladenine；9H-Purine-9-acetic acid, 6-(benzoylamino)-, ethyl ester；ethyl 2-(6-benzamidopurin-9-yl)acetate
• CAS: 171406-46-5
• 化学式: C₁₆H₁₅N₅O₃
• 分子量: 325.327
• InChiKey: UNELGEAKTHZXBR-UHFFFAOYSA-N

物化性质

• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  99
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-N-(benzoyl)-9-(ethoxycarbonylmethyl)adenine 在 NaOH 作用下， 以 水 为溶剂， 以1.4 g (95%)的产率得到9H-嘌呤-9-乙酸,6-(苯甲酰氨基)-
  参考文献：
  名称：

  PEPTIDE NUCLEIC ACID MONOMERS AND OLIGOMERS

  摘要：

  揭示了一种肽核酸单体以及相应的肽核酸分子。该单体包括一个末端氨基团和一个末端基团A。末端氨基团和末端基团A由一个脂肪族基团连接。该脂肪族基团的主链在生理条件下不带电。末端基团A是以下之一：—COOH、—COOR3、—COX、—COSR3、—CN、—CONH2、—CONHR3、—CONR3、R4，其中R3和R4为H或脂肪族、脂环、芳香、芳香脂肪或芳香脂环基团，X为卤素原子。末端氨基团被一个至少有两个碳原子的脂肪族基团取代，可选地含有0到大约2个来自N、O、S、Se和Si组的杂原子。主链具有一个极性头基团Z。

  公开号：

  US20110245458A1
• 作为产物：
  描述：

  苯甲酰氯 在 sodium hydride 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 生成 6-N-(benzoyl)-9-(ethoxycarbonylmethyl)adenine
  参考文献：
  名称：

  PEPTIDE NUCLEIC ACID MONOMERS AND OLIGOMERS

  摘要：

  揭示了一种肽核酸单体以及相应的肽核酸分子。该单体包括一个末端氨基团和一个末端基团A。末端氨基团和末端基团A由一个脂肪族基团连接。该脂肪族基团的主链在生理条件下不带电。末端基团A是以下之一：—COOH、—COOR3、—COX、—COSR3、—CN、—CONH2、—CONHR3、—CONR3、R4，其中R3和R4为H或脂肪族、脂环、芳香、芳香脂肪或芳香脂环基团，X为卤素原子。末端氨基团被一个至少有两个碳原子的脂肪族基团取代，可选地含有0到大约2个来自N、O、S、Se和Si组的杂原子。主链具有一个极性头基团Z。

  公开号：

  US20110245458A1

文献信息

• Building Blocks for Polyamide Nucleic Acids: Facile Synthesis Using Potassium Fluoride Doped Natural Phosphate as Basic Catalyst
  作者：A. Alahiane、M. Taourirte、A. Rochdi、N. Redwane、S. Sebti、J. W. Engels、H. B. Lazrek

  DOI：10.1081/ncn-120019491

  日期：2003.5

  Potassium fluoride doped natural phosphate, inexpensive and environmentally friendly catalyst, is shown to be an efficient basic catalyst for the N1/N9 alkylation of different nucleobases as synthons for PNAs.

  氟化钾掺杂的天然磷酸盐，廉价且环保的催化剂，被证明是用于不同核碱基的N1 / N9烷基化（作为PNA的合成子）的有效碱性催化剂。
• A method for the preparation of nucleic acid binding compound
  申请人：BOEHRINGER MANNHEIM GMBH

  公开号：EP0863150A1

  公开（公告）日：1998-09-09

  A method of the preparation of a nucleic acid binding compound is disclosed wherein a first protecting group removable by a medium strong base and a second protecting group removable by a medium strong acid are used. The synthesis is thereby is increased in recovery yield of a nucleic acid binding compound prepared.

  揭示了一种制备核酸结合化合物的方法，其中使用可由中等强碱去除的第一保护基团和可由中等强酸去除的第二保护基团。因此，合成使得制备的核酸结合化合物的回收产率增加。
• Peptide nucleic acid monomers and oligomers
  申请人：Liu Chuan Fa

  公开号：US08859490B2

  公开（公告）日：2014-10-14

  Disclosed is a peptide nucleic acid monomer as well as a corresponding peptide nucleic acid molecule. The monomer comprises a terminal amino group and a terminal group A. The terminal amino group and the terminal group A are connected by an aliphatic moiety. The main chain of this aliphatic moiety is free of groups that are charged under physiological conditions. The terminal group A is one of —COOH, —COOR3, —COX, —COSR3, —CN, —CONH2, —CONHR3, —CONR3, R4, with R3 and R4 being H or an aliphatic, alicyclic, aromatic, arylaliphatic or arylalicyclic group, and X being a halogen atom. The terminal amino group is substituted by an aliphatic group with a main chain of at least two carbon atoms and optionally 0 to about 2 heteroatoms selected from the group N, O, S, Se and Si. The main chain has a polar head group Z.

  本发明公开了一种肽核酸单体以及相应的肽核酸分子。该单体包括一个末端氨基和一个末端A基团。末端氨基和末端A基团通过一种脂肪基连接。该脂肪基的主链在生理条件下没有带电的基团。末端A基团是以下化学结构之一：—COOH，—COOR3，—COX，—COSR3，—CN，—CONH2，—CONHR3，—CONR3，R4，其中R3和R4为H或脂肪基、脂环基、芳香基、芳基脂基或芳基脂环基，X为卤素原子。末端氨基被一个主链至少含有两个碳原子和可选的0至约2个来自N、O、S、Se和Si的杂原子的脂肪基取代。该主链具有一个极性头基团Z。
• Malakhov, D. V.; Semizarov, D. G.; Yas'ko, M. V., Russian Journal of Bioorganic Chemistry, 1995, vol. 21, # 7, p. 464 - 469
  作者：Malakhov, D. V.、Semizarov, D. G.、Yas'ko, M. V.

  DOI：——

  日期：——
• Acyclic Nucleoside and Nucleotide Analogues with Amide Bond
  作者：E. V. Efimtseva、S. N. Mikhailov、M. V. Jasko、D. V. Malakhov、D. G. Semizarcv、M. V. Fomicheva、E. R. Kern

  DOI：10.1080/15257779508012386

  日期：1995.5.1

  A series of acyclic nucleosides and related alpha-phosphonyl acyclic analogues of dNTP with an amide bond have been prepared. Their antiviral and substrate properties were investigated.New acyclic nucleoside analogues with a rigid structural element, amide bond, have been synthesized in two stages. Alkylation of bis- trimethylsilylated thymine, cytosine and sodium salt of adenine by ethyl bromoacetate gave ethoxycarbonylmethyl derivatives ($) under bar 1a-c. Reaction of ($) under bar 1a-c with aminoalcohols afforded acyclic nucleosides ($) under bar 2-($) under bar 4 in good yields (Scheme 1), These analogues were found to be inactive against HIV-1 (CEM-SS cells) and HSV -1, HSV-2, HCMV, VZV (HFF cells) at concentrations up to 100 mu g/ml and were nontoxic towards CEM and HFF cells. However, it was shown that triphosphate of ($) under bar 2c is incorporated into the DNA chain by DNA polymerase from HSV-1(1). The absence of antiviral activity and cytotoxicity is probably due to the fact that ($) under bar 2-($) under bar 4 are not recognized by cellular and viral kinases.