2'-deoxyformycin A | 40627-14-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-deoxyformycin A
• 英文别名: 2'-deoxyformycin；5-(7-Amino-1H-pyrazolo[4,3-d]pyrimidin-3-yl)-2-hydroxymethyl-tetrahydro-furan-3-ol；(2R,3S,5R)-5-(7-amino-2H-pyrazolo[4,3-d]pyrimidin-3-yl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 40627-14-3
• 化学式: C₁₀H₁₃N₅O₃
• 分子量: 251.245
• InChiKey: OHPIJEVWOFSAIQ-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  130
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2'-deoxyformycin A 在 4-二甲氨基吡啶 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N'-(3-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-1H-pyrazolo[4,3-d]pyrimidin-7-yl)-N,N-dimethyl-formamidine
  参考文献：
  名称：

  Efficient Synthesis of 2'-Deoxyformycin A Containing Oligonucleotides and Characterization of Their Stability in Duplex DNA

  摘要：

  DOI：

  10.1021/jo00127a010
• 作为产物：
  描述：

  7-amino-3-<3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-2'-(phenoxythiocarbonyl)-β-D-ribofuranosyl>pyrazolo<4,3-d>pyrimidine 在 偶氮二异丁腈 、 polymer-supported tin hydride 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.5h， 生成 2'-deoxyformycin A
  参考文献：
  名称：

  Efficient Synthesis of 2'-Deoxyformycin A Containing Oligonucleotides and Characterization of Their Stability in Duplex DNA

  摘要：

  DOI：

  10.1021/jo00127a010

文献信息

• Synthesis of<i>S</i>-Formycinyl-L-homocysteine and Its 3′-Deoxy Derivative
  作者：Paweł Serafinowski

  DOI：10.1055/s-1987-28109

  日期：——

  3′-Deoxyformycin was prepared by transformation of the formycin A with 2-acetoxyisobutyryl bromide. Both formycin A and its 3′-deoxy analogue were converted into their 5′-chloro-5′-deoxy derivatives with thionyl chloride. Finally 5′-chloro-5′-deoxy formycin A and 5′-chloro-3′,5′ dideoxyformycin A were condensed with L-homocysteine sodium salt to give S-formycinyl-L-homocysteine and S-3′-deoxyformycinyl-L-homocysteine in good yields.

  3′-去氧福尔米辛是通过将福尔米辛A与2-乙酸氧异丁酰溴化物反应制备的。福尔米辛A及其3′-去氧类似物均与氯化亚硫酰转化为各自的5′-氯-5′-去氧衍生物。最后，5′-氯-5′-去氧福尔米辛A和5′-氯-3′,5′-二去氧福尔米辛A与L-同型半胱氨酸钠盐缩合，良好收率地得到S-福尔米辛基-L-同型半胱氨酸和S-3′-去氧福尔米辛基-L-同型半胱氨酸。
• Nucleic acid related compounds. 51. Synthesis and biological properties of sugar-modified analogs of the nucleoside antibiotics tubercidin, toyocamycin, sangivamycin, and formycin
  作者：Erik De Clercq、Jan Balzarini、Danuta Madej、Fritz Hansske、Morris J. Robins

  DOI：10.1021/jm00386a007

  日期：1987.3

  antineoplastic, and antimetabolic effects were evaluated for the formycin compounds and 4-amino-7-beta-D-ribofuranosylpyrrolo[2,3-d]pyrimidine (tubercidin), its 5-cyano- (toyocamycin), and 5-carbamoyl-(sangivamycin) antibiotic congeners in comparison with their 2'-deoxy, 3'-deoxy, and arabino analogues. In all cases, the modified-sugar compounds were less cytotoxic than the parent antibiotics. The majority also

  用α-乙酰氧基异丁酰溴处理7-氨基-3-β-D-呋喃核糖基吡唑并[4,3-d]嘧啶（甲霉素），然后将所得反式邻位乙酰氧基溴脱保护，分离出的溴代醇氢解，得到2'-完全脱保护并纯化其盐酸盐后，脱氧-（23％）和3'-脱氧福霉素（32％）。类似的序列产生了3％-脱氧代霉素，和/或3′-脱氧桑奇霉素，约占霉素的产率为80％。评估了甲霉素化合物和4-氨基-7-β-D-呋喃呋喃糖基吡咯并[2,3-d]嘧啶（哌啶），其5-氰基-（托卡霉素）和5-氨基甲酰基的抗病毒，抗肿瘤和抗代谢作用-（sangivamycin）抗生素同类物，与它们的2'-脱氧，3'-脱氧和阿拉伯糖类似物相比。在所有情况下，改性糖化合物的细胞毒性比母体抗生素低。大多数还表现出较低的抗病毒效力。但是，木糖-结核菌素类似物保留了有效的抗疱疹1和2活性，并降低了细胞毒性。标记的代谢物研究表明，这些化合物对RNA和/或蛋白质合成的影响可能比干扰DNA合成更重要。
• Nucleic Acid Related Compounds. 5. The Transformation of Formycin and Tubercidin into 2′- and 3′-Deoxynucleosides
  作者：Morris J. Robins、James R. McCarthy Jr.、Roger A. Jones、Rudolf Mengel

  DOI：10.1139/v73-198

  日期：1973.5.1

  Reaction of tubercidin (4-amino-7-β-D-ribofuranosylpyrrolo[2,3-d]pyrimidine) (1) with α-acetoxyisobutyryl chloride in the presence of excess sodium iodide in acetonitrile gave an acylated iodo intermediate (2) which was converted into 3′-deoxytubercidin (4) by hydrogenolysis and subsequent saponification.Analogous treatment of formycin (7-amino-3-β-D-ribofuranosylpyrazolo[4,3-d]pyrimidine) (5) gave

  结核菌素（4-氨基-7-β-D-呋喃核糖基吡咯并[2,3-d]嘧啶）(1) 与 α-乙酰氧基异丁酰氯在乙腈中过量碘化钠存在下反应得到酰化碘中间体 (2)通过氢解和随后的皂化将其转化为 3'-脱氧结核菌素 (4)。类似处理福尔霉素 (7-amino-3-β-D-ribofuranosylpyrazolo[4,3-d]pyrimidine) (5) 得到 3'-deoxyformycin ( 6) 和 2'-脱氧甲霉素 (7) 的比例约为 3:2。这些纯化的核苷 6 和 7 分别通过酶促脱氨基得到 3'-脱氧甲霉素 B (8) 和 2'-脱氧甲霉素 B(9)。讨论了这些抗生素衍生的脱氧核苷的生物学原理、核磁共振和质谱。
• Improved synthesis of 2'-deoxyformycin A and studies of its in vitro activity against mouse lymphoma of T-cell origin
  作者：Andre Rosowsky、Vishnu C. Solan、Lorraine J. Gudas

  DOI：10.1021/jm00146a020

  日期：1985.8

  7-Amino-3-(2'-deoxy-beta-D-ribofuranosyl)pyrazolo[4,3-d]pyrimidine (2'-deoxyformycin A) was synthesized from formycin A by a sequence consisting of (i) 3',5'-cyclosilylation with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane, (ii) 2'-acylation with phenoxythiocarbonyl chloride and 4-(N,N-dimethylamino)pyridine, (iii) N-trimethylsilylation with hexamethyldisilazane, (iv) reduction of the 2'-O-phenoxythiocarbonyl group with tri-n-butyltin hydride, and (v) desilylation with tetra-n-butylammonium fluoride. 2'-Deoxyformycin A was a potent inhibitor of the in vitro growth of S49 lymphoma, a murine tumor of T-cell origin. The IC50 of 2'-deoxyformycin A against S49 cells was 10-15 microM, whereas that of 2'-deoxyadenosine (dAdo) under the same conditions (72-h incubation in medium containing heat-inactivated horse serum) was 180 microM. In the presence of 10 microM erythro-9-(2-hydroxy-3-nonyl)adenine (EHNA) to block intracellular adenosine deaminase (ADA) activity, 2'-deoxyformycin A and dAdo both gave IC50's of 5-10 microM. When assayed against a mutant S49 subline lacking adenosine kinase (AK) or a subline with a combined deletion of AK and deoxycytidine kinase (dCK), 2'-deoxyformycin A in combination with 10 microM EHNA was inactive at concentrations of up to 50 microM. Similar lack of activity against kinase-deficient cells was shown by formycin A. Thus, phosphorylation of 2'-deoxyformycin A appears to be required for biological activity and is probably catalyzed by AK rather than dCK. 2'-Deoxyformycin A and related 2'-deoxyribo-C-nucleoside analogues of the purine type may be of interest as potential T-cell specific cytotoxic agents.
• Reactions of 2-acyloxyisobutyryl halides with nucleosides. III. Reactions of tubercidin and formycin
  作者：Tikam C. Jain、Alan F. Russell、John G. Moffatt

  DOI：10.1021/jo00958a023

  日期：1973.9