1-[(benzyloxy)methyl]-3-[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-pyrrole-2,5-dione | 480434-58-0

• 分子结构分类: 有机化合物
• 英文名称: 1-[(benzyloxy)methyl]-3-[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-pyrrole-2,5-dione
• 英文别名: 1-[(benzyloxy)methyl]-3-[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-pyrrolo[2,3-b]pyrid-3-yl]-4-(1H-pyrrolo[2,3-b]pyrid-3-yl)-1H-pyrrole-2,5-dione；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[3-[2,5-dioxo-1-(phenylmethoxymethyl)-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrrol-3-yl]pyrrolo[2,3-b]pyridin-1-yl]oxan-2-yl]methyl acetate
• CAS: 480434-58-0
• 化学式: C₄₀H₃₇N₅O₁₂
• 分子量: 779.76
• InChiKey: OQOQVPLDHRWTFN-IKHVBDJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  208
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  1-[(benzyloxy)methyl]-3-[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-pyrrole-2,5-dione 在 碘 作用下， 以 苯 为溶剂， 反应 1.5h， 以76%的产率得到6-[(benzyloxy)methyl]-12-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-12,13-dihydro-5H-pyrido[2,3-b]pyrido[3',2':4,5]pyrrolo[3,2-g]pyrrolo[3,4-e]indole-5,7(6H)-dione
  参考文献：
  名称：

  Syntheses and antiproliferative activities of rebeccamycin analogues bearing two 7-azaindole moieties

  摘要：

  As a part of structure activity relationship studies on rebeccamycin analogues, compounds containing two aza-indole moieties were synthesized bearing either a methyl group or a hydrogen atom on the imide nitrogen. The azaindole substructures were expected to enhance the cytotoxicity toward tumor cell lines through stronger hydrogen bonding with the target enzyme(s). The cytotoxicities of compounds 8, 10 and 19 against a panel of tumor cell lines were examined and compared with those of rebeccamycin, dechlorinated rebeccamycin 2 and N-methylated analogue A. Their effect on the L1210 cell cycle was also evaluated. Compound 19, having an imide NH function had the strongest cytotoxicity towards L1210 cells and induced the largest accumulation of cells in the G2 + M phases of the cell cycle. In contrast to their non-aza analogues, which were cytotoxic for all the cell lines tested, diaza compounds 10 and 19 showed selectivity for some cell lines. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00532-1
• 作为产物：
  描述：

  1-[(benzyloxy)methyl]-3-[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-4-[1-(phenylsulphonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-1H-pyrrole-2,5-dione 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以76%的产率得到1-[(benzyloxy)methyl]-3-[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Syntheses and antiproliferative activities of rebeccamycin analogues bearing two 7-azaindole moieties

  摘要：

  As a part of structure activity relationship studies on rebeccamycin analogues, compounds containing two aza-indole moieties were synthesized bearing either a methyl group or a hydrogen atom on the imide nitrogen. The azaindole substructures were expected to enhance the cytotoxicity toward tumor cell lines through stronger hydrogen bonding with the target enzyme(s). The cytotoxicities of compounds 8, 10 and 19 against a panel of tumor cell lines were examined and compared with those of rebeccamycin, dechlorinated rebeccamycin 2 and N-methylated analogue A. Their effect on the L1210 cell cycle was also evaluated. Compound 19, having an imide NH function had the strongest cytotoxicity towards L1210 cells and induced the largest accumulation of cells in the G2 + M phases of the cell cycle. In contrast to their non-aza analogues, which were cytotoxic for all the cell lines tested, diaza compounds 10 and 19 showed selectivity for some cell lines. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00532-1

文献信息

• Pyrido-pyrido-pyrrolo pyrrolo-indole and pyrido-pyrrolo pyrrolo carbazole derivatives, method for the production thereof and pharmaceutical compositions containing said derivatives
  申请人：——

  公开号：US20040152721A1

  公开（公告）日：2004-08-05

  Compounds of formula (I): 1 wherein: W 1 and W 2 , together with the carbon atoms to which they are bonded, represent a phenyl group or a pyridyl group, and at least one of the groups W 1 or W 2 represents a pyridyl group, R 1 and R 2 each represent a group of formula U-V as defined in the description, X and X 1 each represent a hydrogen atom or a hydroxy, alkoxy, mercapto or alkylthio group, Y and Y 1 each represent a hydrogen atom, or X and Y, X 1 and Y 1 , together with the carbon atom carrying them, represent a carbonyl or thiocarbonyl group, R 4 and R 5 are as defined in the description, Q 1 , Q 2 represent a hydrogen atom, or Q 1 and Q 2 , together with the carbon atoms carrying them, form an aromatic bond. Medicaments.

  式(I)的化合物：其中：W1和W2与它们连接的碳原子一起表示苯基或吡啶基，且W1或W2中至少一个表示吡啶基，R1和R2分别表示如描述中所定义的U-V式的基团，X和X1分别表示氢原子或羟基、烷氧基、巯基或烷硫基，Y和Y1分别表示氢原子，或X和Y、X1和Y1连同携带它们的碳原子表示羰基或硫代羰基，R4和R5如描述中所定义，Q1、Q2表示氢原子，或Q1和Q2连同携带它们的碳原子形成芳香键。药物。
• US7001906B2
  申请人：——

  公开号：US7001906B2

  公开（公告）日：2006-02-21