2'-脱氧桑吉瓦霉素 | 83379-28-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2'-脱氧桑吉瓦霉素
• 英文名称: 4-amino-5-carboxamido-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
• 英文别名: 2’-deoxysangivamycin；2'-deoxysangivamycin；4-amino-7-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carboxamide
• CAS: 83379-28-6
• 化学式: C₁₂H₁₅N₅O₄
• 分子量: 293.282
• InChiKey: SSAXPGYDNCGRHY-XLPZGREQSA-N

物化性质

• 沸点：
  763.7±60.0 °C(Predicted)
• 密度：
  1.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  150
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2'-脱氧桑吉瓦霉素 在 二溴亚砜 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 15.0h， 以72%的产率得到5'-bromo carboxamide-pyrrolopyrimidine
  参考文献：
  名称：

  Ismail, E. S.; Islam, L. E.; Abbasi, M. M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 8, p. 535 - 537

  摘要：

  DOI：
• 作为产物：
  描述：

  4-amino-5-cyano-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 在 ammonium hydroxide 、 双氧水 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 12.0h， 以75%的产率得到2'-脱氧桑吉瓦霉素
  参考文献：
  名称：

  通过立体有择的钠盐糖基化方法制备的吡咯前体的2'-脱氧代霉素，2'-脱氧桑奇霉素和相关的7-β-阿拉伯呋喃糖基吡咯并[2,3- ]嘧啶环的全合成

  摘要：

  首次完成了完全芳香的吡咯，2-溴-（或乙硫基）-5-乙氧基亚甲基氨基-吡咯-3、4-二碳腈（和）的立体有择的高产糖基化反应。用1-氯-2-脱氧-3.5-二-甲苯甲酰基-α--赤型五呋喃糖（）或用其处理的钠盐仅产生相应的具有β-端基异构构型（和）的封闭核苷，其在环上闭合和进一步的官能团转化提供了2'-脱氧代霉素（）和2'-脱氧桑格霉素（）的总合成。1-氯-2,3,5-三-苄基-α-呋喃糖的钠盐的类似糖基化作用（）提供相应的封闭核苷（），其在闭环时脱溴/去苄基化，得到4-氨基-7-β-阿拉伯呋喃糖基吡咯并[2,3- ]嘧啶-5-甲酰胺（）。已证明该糖基化方法可用于其他饱和吡咯，吡咯-3-甲腈（）和3,4-吡咯二羧酸二乙酯（）的合成实用性。

  DOI：

  10.1016/s0040-4020(01)96068-5

文献信息

• Nucleic acid related compounds. 42. A general procedure for the efficient deoxygenation of secondary alcohols. Regiospecific and stereoselective conversion of ribonucleosides to 2'-deoxynucleosides
  作者：Morris J. Robins、John S. Wilson、Fritz Hansske

  DOI：10.1021/ja00350a052

  日期：1983.6
• Incorporation of 2′-Deoxysangivamycin in DNA Duplexes: The Conversion of a Pyrrolo[2, 3-<i>d</i>]Pyrimidine Nitrile to a Carboxamide upon Oligonucleotide Deprotection
  作者：Frank Seela、Matthias Zulauf

  DOI：10.1080/07328319908044635

  日期：1999.11

  Oligonucleotides containing 2'-deoxysangivamycin are described. The phosphoramidite of 2'-deoxytoyocamycin was prepared and used in solid-phase synthesis. Upon deprotection the pyrrolo[2,3-d]pyrimidine nitrile residues were converted to carboxamides. According to the T-m-measurements the 7-carboxamido group of the 7-deazaadenine moiety stabilizes the DNA duplex significantly.
• [EN] COMPOSITIONS AND METHODS FOR EDITING NUCLEIC ACIDS IN CELLS UTILIZING OLIGONUCLEOTIDES<br/>[FR] COMPOSITIONS ET PROCÉDÉS D'ÉDITION D'ACIDES NUCLÉIQUES DANS DES CELLULES À L'AIDE D'OLIGONUCLÉOTIDES
  申请人：WOOLF TOD M

  公开号：WO2016094845A3

  公开（公告）日：2017-06-15
• Pyrrolopyrimidine nucleosides. 18, Synthesis and chemotherapeutic activity of 4-amino-7-(3-deoxy-.beta.-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carboxamide (3'-deoxysangivamycin) and 4-amino-7-(2-deoxy-.beta.-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carboxamide (2'-deoxysangivamycin)
  作者：Tokumi Maruyama、Linda L. Wotring、Leroy B. Townsend

  DOI：10.1021/jm00355a006

  日期：1983.1

  A multistep synthesis, using the nucleoside antibiotic toyocamycin as the starting material, has furnished 6,2'-S-cyclosangivamycin (6). Desulfurization of 6,2'-S-cyclosangivamycin (6) with Raney nickel has provided 2'-deoxysangivamycin (7). Treatment of sangivamycin (1c) with sodium iodide and alpha-acetoxyisobutyryl chloride has furnished 4-amino-7-[2-O-acetyl-3-deoxy-3-iodo-5-O-(2,5,5-trimethyl-4-oxo-1, 3-dioxolan-2-yl)-beta-D-xylofuranosyl]-pyrrolo[2,3-d] pyrimidine-5-carboxamide (8a). Dehalogenation of 8a with 10% palladium on charcoal was followed by a removal of the blocking groups with ammonium hydroxide to give 3'-deoxysangivamycin (9) in 49% overall yield. The reaction of sangivamycin (1c) with diphenyl disulfide and tributylphosphine gave 5'-(phenylthio)-5'-deoxysangivamycin (10). Treatment of 10 with Raney Nickel afforded 5'-deoxysangivamycin (11). Antitumor evaluation showed that 3'-deoxysangivamycin had significant activity against the murine leukemia L1210 both in vivo and in vitro, although it was less potent on a molar basis than the parent compound sangivamycin. The 2'- and 5'-deoxysangivamycins did not show significant antitumor activity.
• [EN] METHOD FOR TREATING POXVIRIDAE INFECTIONS<br/>[FR] MÉTHODES DE TRAITEMENT D'INFECTIONS À POXVIRIDAE
  申请人：OYAGEN INC

  公开号：WO2021211759A1

  公开（公告）日：2021-10-21

  Disclosed herein are methods, compositions and kits for treating and inhibiting Poxviridae virus infections, for example, Vaccinia virus infections. Further disclosed are stop- gap methods for controlling the spread of Poxviridae virus infections.