3-acetamido-4-chlorobenzyl-β-maltoside | 269734-49-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetamido-4-chlorobenzyl-β-maltoside
• 英文别名: N-[2-chloro-5-(β-D-maltosyloxymethyl)phenyl]acetamide；N-[2-chloro-5-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]phenyl]acetamide
• CAS: 269734-49-8
• 化学式: C₂₁H₃₀ClNO₁₂
• 分子量: 523.922
• InChiKey: WMPWGSHJOBZBJA-ZESVGKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  208
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-acetamido-4-chlorobenzyl-β-maltoside 在 2,3,5-三甲基吡啶 、 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(2R,3S,4R,5R,6R)-3-[[(2R,4aR,6R,7R,8R,8aS)-2-benzyl-7,8-dihydroxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-6-[(3-acetamido-4-chlorophenyl)methoxy]-4,5-dihydroxyoxan-2-yl]methyl benzoate
  参考文献：
  名称：

  Stability studies of C-4′,6′ acetal benzylmaltosides synthesized as inhibitors of smooth muscle cell proliferation

  摘要：

  In our investigations to synthesize inhibitors of smooth muscle cell (SMC) proliferation, compound 6a displayed sub-micromolar activity in in vitro antiproliferative assays and reduced intimal thickening using a rat balloon angioplasty model via iv administration. In order to identify analogs that could be administered orally, the chemical instability of the C-4',6' acetal of compound 6a was addressed. Several novel variants with increased acid stability and comparable in vitro activity were prepared. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.049
• 作为产物：
  描述：

  4-氯-3-硝基苯甲醇 在 甲醇 、 sodium methylate 、 氰化汞 、 三乙胺 、 mercury dibromide 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 乙酸乙酯 、 乙腈 为溶剂， 反应 29.5h， 生成 3-acetamido-4-chlorobenzyl-β-maltoside
  参考文献：
  名称：

  Stability studies of C-4′,6′ acetal benzylmaltosides synthesized as inhibitors of smooth muscle cell proliferation

  摘要：

  In our investigations to synthesize inhibitors of smooth muscle cell (SMC) proliferation, compound 6a displayed sub-micromolar activity in in vitro antiproliferative assays and reduced intimal thickening using a rat balloon angioplasty model via iv administration. In order to identify analogs that could be administered orally, the chemical instability of the C-4',6' acetal of compound 6a was addressed. Several novel variants with increased acid stability and comparable in vitro activity were prepared. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.049

文献信息

• Acetal benzylmaltosides as inhibitors of smooth muscle cell proliferation
  申请人：American Home Products Corporation

  公开号：US06340670B1

  公开（公告）日：2002-01-22

  This invention provides smooth muscle cell proliferation inhibitors of formula I having the structure with the variables defined herein.

  本发明提供了具有本文定义的变量结构的式I平滑肌细胞增殖抑制剂。
• Acylated benzylmaltosides as inhibitors of smooth muscle cell proliferation
  申请人：Mayer C. Scott

  公开号：US20050176652A1

  公开（公告）日：2005-08-11

  This invention provides smooth muscle cell proliferation inhibitors of formula I having the structure wherein R 1 , R 2 , R 3 , R 4 , and R 5 are each, independently, hydrogen, acyl of 2-7 carbon atoms, haloacyl of 2-7 carbon atoms, nitroacyl of 2-7 carbon atoms, cyanoacyl of 2-7 carbon atoms, trifluoromethylacyl of 3-8 carbon atoms, or benzoyl in which the phenyl moiety is substituted with R 8 ; R 6 and R 7 are each, independently, —OH, —OR 9 , O-tert-butyldimethylsilyl, O-trialkylsilyl of 1-6 carbon atoms per alkyl moiety, O-triphenylsilyl, R 8 , R 10 , R 11 , and R 12 are each, independently, hydrogen, —CN, —NO 2 , halogen, CF 3 , alkyl of 1-6 carbon atoms, acetyl, benzoyl, or alkoxy of 1-6 carbon atoms; R 9 is acyl of 2-7 carbon atoms, haloacyl of 2-7 carbon atoms, nitroacyl of 2-7 carbon atoms, cyanoacyl of 2-7 carbon atoms, trifluoromethylacyl of 3-8 carbon atoms, or benzoyl in which the phenyl moiety is substituted with R 8 ; Y is O, S, NH, NMe, or CH 2 ; W is halogen, —CN, CF 3 , alkyl of 1-6 carbon atoms, haloalkyl of 1-6 carbon atoms, nitroalkyl of 1-6 carbon atoms, cyanoalkyl of 1-6 carbon atoms, alkoxyalkyl of 2-12 carbon atoms, alkoxy of 1-6 carbon atoms, or phenyl mono-, di-, or tri-substituted with R 8 ; Z is —NO 2 , —NH 2 , —NHR 13 , or —NHCO-Het; R 13 is acyl of 2-7 carbon atoms, haloacyl of 2-7 carbon atoms, nitroacyl of 2-7 carbon atoms, cyanoacyl of 2-7 carbon atoms, trifluoromethylacyl of 3-8 carbon atoms, benzoyl in which the phenyl moiety is substituted with R 8 , or R 13 is an α-amino acid in which the a carboxyl group forms an amide with the nitrogen of Z, wherein if said amino acid is glutamic acid or aspartic acid, the non-α carboxylic acid is an alkyl ester in which the alkyl moiety contains from 1-6 carbon atoms; Het is pyridyl substituted with R 8 , thienyl substituted with R 8 , furyl substituted with R 8 , oxazolyl substituted with R 8 , pyrazinyl substituted with R 8 , pyrimidinyl substituted with R 8 , or thiazolyl substituted with R 8 ; R 14 is R 8 , —NH 2 , —CO 2 H, or —NH-acyl of 2-7 carbon atoms; n=0-3; with the proviso that when Z is —NHR 13 and Y is O, at least one of R 1 , R 2 , R 3 , R 4 , and R 5 is hydrogen, or at least one of R 6 and R 7 is OH, or a pharmaceutically acceptable salt thereof.

  本发明提供具有结构式I的平滑肌细胞增殖抑制剂，其中R1、R2、R3、R4和R5各自独立地为氢、2-7个碳原子的酰基、2-7个碳原子的卤代酰基、2-7个碳原子的硝基酰基、2-7个碳原子的氰基酰基、3-8个碳原子的三氟甲基酰基或苯甲酰基，其中苯基部分被R8取代；R6和R7各自独立地为-OH、-OR9、O-叔丁基二甲基硅烷基、1-6个碳原子的三烷基硅基或三苯基硅基；R8、R10、R11和R12各自独立地为氢、-CN、-NO2、卤素、CF3、1-6个碳原子的烷基、乙酰基、苯甲酰基或1-6个碳原子的烷氧基；R9为2-7个碳原子的酰基、2-7个碳原子的卤代酰基、2-7个碳原子的硝基酰基、2-7个碳原子的氰基酰基、3-8个碳原子的三氟甲基酰基或苯甲酰基，其中苯基部分被R8取代；Y为O、S、NH、NMe或CH2；W为卤素、-CN、CF3、1-6个碳原子的烷基、1-6个碳原子的卤代烷基、1-6个碳原子的硝基烷基、1-6个碳原子的氰基烷基、2-12个碳原子的烷氧基、1-6个碳原子的烷氧基或苯基单、二或三取代的R8；Z为-NO2、-NH2、-NHR13或-NHCO-Het；R13为2-7个碳原子的酰基、2-7个碳原子的卤代酰基、2-7个碳原子的硝基酰基、2-7个碳原子的氰基酰基、3-8个碳原子的三氟甲基酰基、苯甲酰基，其中苯基部分被R8取代，或者R13是α-氨基酸，其中α-羧基与Z的氮形成酰胺，如果该氨基酸是谷氨酸或天冬氨酸，则非α-羧酸是含有1-6个碳原子的烷基酯；Het是被R8取代的吡啶基、噻吩基、呋喃基、噁唑基、吡嗪基、嘧啶基或噻唑基；R14为R8、-NH2、-CO2H或2-7个碳原子的-NH-酰基；n=0-3；条件是，当Z为-NHR13且Y为O时，R1、R2、R3、R4和R5中至少有一个为氢，或R6和R7中至少有一个为-OH，或其药学上可接受的盐。
• Stability studies of C-4′,6′ acetal benzylmaltosides synthesized as inhibitors of smooth muscle cell proliferation
  作者：Scott C. Mayer、William Gallaway、John Kulishoff、Maisheng Yin、Vidya Gadamasetti、Robert Mitchell

  DOI：10.1016/j.bmcl.2004.03.049

  日期：2004.6

  In our investigations to synthesize inhibitors of smooth muscle cell (SMC) proliferation, compound 6a displayed sub-micromolar activity in in vitro antiproliferative assays and reduced intimal thickening using a rat balloon angioplasty model via iv administration. In order to identify analogs that could be administered orally, the chemical instability of the C-4',6' acetal of compound 6a was addressed. Several novel variants with increased acid stability and comparable in vitro activity were prepared. (C) 2004 Elsevier Ltd. All rights reserved.