9-[(3aR,4R,6R,6aR)-6-(methoxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-6-chloropurine | 223756-63-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 9-[(3aR,4R,6R,6aR)-6-(methoxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-6-chloropurine
• CAS: 223756-63-6
• 化学式: C₁₄H₁₇ClN₄O₄
• 分子量: 340.766
• InChiKey: LJCPHIRBAFJEKG-QYVSTXNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  80.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  9-[(3aR,4R,6R,6aR)-6-(methoxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-6-chloropurine 在 ammonium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 1.5h， 以57%的产率得到2'-O,3'-O-isopropylidene-5'-O-methyladenosine
  参考文献：
  名称：

  Novel Adenosine-Derived Inhibitors of 70 kDa Heat Shock Protein, Discovered Through Structure-Based Design

  摘要：

  The design and synthesis of novel adenosine-derived inhibitors of HSP70, guided by modeling and X-ray crystallographic structures of these compounds in complex with HSC70/BAG-1, is described. Examples exhibited submicromolar affinity for HSP70, were highly selective over HSP90, and some displayed potency against HCT116 cells. Exposure of compound 12 to HCT116 cells caused significant reduction in cellular levels of Raf-1 and Her2 at concentrations similar to that which caused cell growth arrest.

  DOI：

  10.1021/jm801627a
• 作为产物：
  描述：

  溴甲烷 、 6-氯-9-beta-D-(2,3-异亚丙基)呋喃核糖基嘌呤 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.5h， 以85%的产率得到9-[(3aR,4R,6R,6aR)-6-(methoxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-6-chloropurine
  参考文献：
  名称：

  Novel Adenosine-Derived Inhibitors of 70 kDa Heat Shock Protein, Discovered Through Structure-Based Design

  摘要：

  The design and synthesis of novel adenosine-derived inhibitors of HSP70, guided by modeling and X-ray crystallographic structures of these compounds in complex with HSC70/BAG-1, is described. Examples exhibited submicromolar affinity for HSP70, were highly selective over HSP90, and some displayed potency against HCT116 cells. Exposure of compound 12 to HCT116 cells caused significant reduction in cellular levels of Raf-1 and Her2 at concentrations similar to that which caused cell growth arrest.

  DOI：

  10.1021/jm801627a

文献信息

• Chemical compounds
  申请人：SmithKline Beecham Corporation

  公开号：US20030158146A1

  公开（公告）日：2003-08-21

  A compound of formula (I), wherein R 2 represents C 1-3 alkyl, halogen or hydrogen; R 3 represents straight or branched alkyl group of 1-6 carbon atoms; with the proviso that, when R 3 represents C 1-3 alkyl, R 2 represents C 1-3 alkyl, R 1 cannot represent phenyl optionally substituted by one or more substituents selected from halogen, C 1-3 alkyl, trifluoromethyl, nitro, cyano, —CO 2 R c , —CONR c R d , —COR c , —SOR e , —SO 2 R e , —SO 3 H, —SO 2 NR c R d , —OR c , —NHSO 2 R e , —NHCOR c and —NR c R d ; and salts and solvates thereof, in particular, physiologically acceptable solvates and salts thereof. These compounds are agonists at the Adenosine A1 receptor.

  式 (I) 的化合物，其中 R 2 代表 C 1-3 烷基、卤素或氢；R 3 代表 1-6 个碳原子的直链或支链烷基；但当 R 3 代表 C 1-3 烷基时，R 2 代表 C 1-3 烷基，R 1 不能代表被一个或多个取代基任选取代的苯基，这些取代基选自卤素、C 1-3 烷基、三氟甲基、硝基、氰基、-CO 2 R c 、-CONR c R d , -COR c , -SOR e , -SO 2 R e ，-SO 3 H, -SO 2 NR c R d ，-OR c , -NHSO 2 R e , -NHCOR c 和-NR c R d 及其盐和溶剂，特别是生理上可接受的溶剂和盐。这些化合物是腺苷 A1 受体的激动剂。
• ADENOSINE A1 RECEPTOR AGONISTS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1030856A2

  公开（公告）日：2000-08-30
• US6544960B1
  申请人：——

  公开号：US6544960B1

  公开（公告）日：2003-04-08
• US6740644B2
  申请人：——

  公开号：US6740644B2

  公开（公告）日：2004-05-25
• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSES CHIMIQUES
  申请人：——

  公开号：WO1999024451A2

  公开（公告）日：1999-05-20

  [EN] A compound of formula (I), wherein R<2> represents C1-3alkyl, halogen or hydrogen; R<3> represents straight or branched alkyl group of 1-6 carbon atoms; with the proviso that, when R<3> represents C1-3alkyl, R<2> represents C1-3alkyl, R<1> cannot represent phenyl optionally substituted by one or more substituents selected from halogen, C1-3alkyl, trifluoromethyl, nitro, cyano, -CO2R, -CONRR, -COR, -SOR, -SO2R, -SO3H, -SO2NRR, -OR, -NHSO2R, -NHCOR and -NRR; and salts and solvates thereof, in particular, physiologically acceptable solvates and salts thereof. These compounds are agonists at the Adenosine A1 receptor.
  [FR] L'invention concerne un composé de la formule (I) où: R<2> est alkyle C1-3, halogène, hydrogène; R<3> est un groupe alkyle droit ou ramifié de 1-6 atomes de carbone; à condition que, lorsque R<3> représente alkyle C1-6, R<2> représente alkyle C1-3, R<1> ne peut pas représenter phényle éventuellement substitué au choix par un ou plusieurs substituants choisis parmi halogène, alkyle C1-3, trifluorométhyle, nitro, cyano, -CO2R, -CONRR, -COR, -SOR, -SO2R, -SO3H, -SO2NRR, -OR, -NHSO2R, -NHCOR et -NRR; cette invention se rapportant également à des sels et solvates de ce composé, en particulier à des sels et solvates physiologiquement acceptables. Ces composés sont des antagonistes du récepteur A1 de l'adénosine.