4-Amino-6-chloro-1-β-D-ribofuranosylpyrrolo<3,2-c>pyridine | 120446-77-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Amino-6-chloro-1-β-D-ribofuranosylpyrrolo<3,2-c>pyridine
• 英文别名: (2R,3R,4S,5R)-2-(4-amino-6-chloropyrrolo[3,2-c]pyridin-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 120446-77-7
• 化学式: C₁₂H₁₄ClN₃O₄
• 分子量: 299.714
• InChiKey: SWQBPMZNYWNIEV-UGKPPGOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  114
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-Amino-6-chloro-1-β-D-ribofuranosylpyrrolo<3,2-c>pyridine 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以81%的产率得到4-Amino-1-β-D-ribofuranosylpyrrolo<3,2-c>pyridine
  参考文献：
  名称：

  3,7-Dideazapurine nucleosides. Synthesis and antitumor activity of 1-deazatubercidin and 2-chloro-2'-deoxy-3,7-dideazaadenosine

  摘要：

  1-Deazatubercidin (5) has been synthesized by glycosylation of the anion of 4,6-dichloro-1H-pyrrolo[3,2-c]pyridine (9) with 1-chloro-2,3-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-alpha-D-r ibofuranos e (12). The reaction gave a mixture of blocked nucleosides with beta- and alpha-configuration (13a and 13b). Deprotection of 13a provided 4,6-dichloro-1-beta-D-ribofuranosylpyrrolo[3,2-c]pyridine (14), which on treatment with hydrazine, followed by reduction of the resulting 4-hydrazino compound with Raney nickel, gave 4-amino-6-chloro-1-beta-D-ribofuranosylpyrrolo[3,2-c]pyridine (15), 1-deazatubercidin, and a small quantity of 4,6-diamino-1-beta-D-ribofuranosylpyrrolo[3,2-c]pyridine (16). Dehalogenation of 15 provided another route to 5. 2-Chloro-2'-deoxy-3,7-dideazaadenosine (6) together with 2'-deoxy-3,7-dideazaadenosine (18) was obtained by hydrazinolysis of 4,6-dichloro-1-(2-deoxy-beta-D-erythro-pentofuranosyl)pyrrolo- [3,2-c]pyridine (17), followed by reduction of the resulting 4-hydrazino compound. Nucleosides 5, 6, 15, and 18 are devoid of any significant antitumor activity in vitro. Compound 16 showed significant activity against P388 leukemia in cell culture.

  DOI：

  10.1021/jm00127a011
• 作为产物：
  描述：

  4,6-Dichloro-1-<2,3-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>pyrrolo<3,2-c>pyridine 在 镍 、 一水合肼 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 7.17h， 生成 4-Amino-6-chloro-1-β-D-ribofuranosylpyrrolo<3,2-c>pyridine
  参考文献：
  名称：

  3,7-Dideazapurine nucleosides. Synthesis and antitumor activity of 1-deazatubercidin and 2-chloro-2'-deoxy-3,7-dideazaadenosine

  摘要：

  1-Deazatubercidin (5) has been synthesized by glycosylation of the anion of 4,6-dichloro-1H-pyrrolo[3,2-c]pyridine (9) with 1-chloro-2,3-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-alpha-D-r ibofuranos e (12). The reaction gave a mixture of blocked nucleosides with beta- and alpha-configuration (13a and 13b). Deprotection of 13a provided 4,6-dichloro-1-beta-D-ribofuranosylpyrrolo[3,2-c]pyridine (14), which on treatment with hydrazine, followed by reduction of the resulting 4-hydrazino compound with Raney nickel, gave 4-amino-6-chloro-1-beta-D-ribofuranosylpyrrolo[3,2-c]pyridine (15), 1-deazatubercidin, and a small quantity of 4,6-diamino-1-beta-D-ribofuranosylpyrrolo[3,2-c]pyridine (16). Dehalogenation of 15 provided another route to 5. 2-Chloro-2'-deoxy-3,7-dideazaadenosine (6) together with 2'-deoxy-3,7-dideazaadenosine (18) was obtained by hydrazinolysis of 4,6-dichloro-1-(2-deoxy-beta-D-erythro-pentofuranosyl)pyrrolo- [3,2-c]pyridine (17), followed by reduction of the resulting 4-hydrazino compound. Nucleosides 5, 6, 15, and 18 are devoid of any significant antitumor activity in vitro. Compound 16 showed significant activity against P388 leukemia in cell culture.

  DOI：

  10.1021/jm00127a011

文献信息

• FRANCHETTI, P.;CRISTALLI, G.;GRIFANTINI, M.;NASINI, E.;VITTORI, S., NUCLEOSIDES AND NUCLEOTIDES, 8,(1989) N-6, C. 1143-1144
  作者：FRANCHETTI, P.、CRISTALLI, G.、GRIFANTINI, M.、NASINI, E.、VITTORI, S.

  DOI：——

  日期：——
• CRISTALLI, GLORIA;FRANCHETTI, PALMARISA;GRIFANTINI, MARIO;NOCENTINI, GIUS+, J. MED. CHEM., 32,(1989) N, C. 1463-1466
  作者：CRISTALLI, GLORIA、FRANCHETTI, PALMARISA、GRIFANTINI, MARIO、NOCENTINI, GIUS+

  DOI：——

  日期：——
• 3,7-Dideazapurine nucleosides. Synthesis and antitumor activity of 1-deazatubercidin and 2-chloro-2'-deoxy-3,7-dideazaadenosine
  作者：Gloria Cristalli、Palmarisa Franchetti、M. Grifantini、Giuseppe Nocentini、Sauro Vittori

  DOI：10.1021/jm00127a011

  日期：1989.7

  1-Deazatubercidin (5) has been synthesized by glycosylation of the anion of 4,6-dichloro-1H-pyrrolo[3,2-c]pyridine (9) with 1-chloro-2,3-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-alpha-D-r ibofuranos e (12). The reaction gave a mixture of blocked nucleosides with beta- and alpha-configuration (13a and 13b). Deprotection of 13a provided 4,6-dichloro-1-beta-D-ribofuranosylpyrrolo[3,2-c]pyridine (14), which on treatment with hydrazine, followed by reduction of the resulting 4-hydrazino compound with Raney nickel, gave 4-amino-6-chloro-1-beta-D-ribofuranosylpyrrolo[3,2-c]pyridine (15), 1-deazatubercidin, and a small quantity of 4,6-diamino-1-beta-D-ribofuranosylpyrrolo[3,2-c]pyridine (16). Dehalogenation of 15 provided another route to 5. 2-Chloro-2'-deoxy-3,7-dideazaadenosine (6) together with 2'-deoxy-3,7-dideazaadenosine (18) was obtained by hydrazinolysis of 4,6-dichloro-1-(2-deoxy-beta-D-erythro-pentofuranosyl)pyrrolo- [3,2-c]pyridine (17), followed by reduction of the resulting 4-hydrazino compound. Nucleosides 5, 6, 15, and 18 are devoid of any significant antitumor activity in vitro. Compound 16 showed significant activity against P388 leukemia in cell culture.