1-(hex-5-enyl)-3,7-dimethylxanthine | 58999-18-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 1-(hex-5-enyl)-3,7-dimethylxanthine
• 英文别名: 1-(hex-5-enyl)-3,7-dimethyl-1H-purine-2,6(2H,6H)-dione；1-(5-hexenyl)-3,7-dimethylxanthine；1-(6-hexenyl)-3,7-dimethylxanthine；1-(Hex-5-en-1-yl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione；1-hex-5-enyl-3,7-dimethylpurine-2,6-dione
• CAS: 58999-18-1
• 化学式: C₁₃H₁₈N₄O₂
• 分子量: 262.312
• InChiKey: LZRTZRBKFZHHQT-UHFFFAOYSA-N

物化性质

• 沸点：
  471.1±47.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(hex-5-enyl)-3,7-dimethylxanthine 、 sodium hydrogensulfite 在 m-chloroperoxybenzoic acid 作用下， 以 二氯甲烷 为溶剂， 生成 1-(5,6-oxidohexyl)-3,7-dimethylxanthine
  参考文献：
  名称：

  Substituted epoxyalkyl xanthines

  摘要：

  式为##STR1##的化合物包括已分离的对映体和/或非对映体和它们的混合物，其中一个或两个R各自独立地为##STR2##其中n为1-16，R'为H或烷基(1-4C)；其余的每个R各自独立地为H，烷基(1-6C)，烯基(1-6C)或苄基；其中所述的烷基或烯基可以被羟基，卤素或二甲氨基基团取代，并/或被氧原子中断；这些化合物在调节细胞对内部和外部刺激的影响方面是有用的，通过逆转这些刺激对细胞短期次级信使途径的影响。特别地，这些化合物在主要刺激和它们与这些细胞的接触后几秒钟内降低了来源于所述PA的不饱和非花生酸磷脂酸(PA)和二酰甘油(DAG)的升高水平。调节效应取决于目标细胞的性质和应用的刺激。

  公开号：

  US05288721A1
• 作为产物：
  描述：

  可可碱 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 0.33h， 以87%的产率得到1-(hex-5-enyl)-3,7-dimethylxanthine
  参考文献：
  名称：

  Predictable Stereoselective and Chemoselective Hydroxylations and Epoxidations with P450 3A4

  摘要：

  Enantioselective hydroxylation of one specific methylene in the presence of many similar groups is debatably the most challenging chemical transformation. Although chemists have recently made progress toward the hydroxylation of inactivated C-H bonds, enzymes such as P450s (CYPs) remain unsurpassed in specificity and scope. The substrate promiscuity of many P450s is desirable for synthetic applications; however, the inability to predict the products of these enzymatic reactions is impeding advancement. We demonstrate here the utility of a chemical auxiliary to control the selectivity of CYP3A4 reactions. When linked to substrates, inexpensive, achiral theobromine directs the reaction to produce hydroxylation or epoxidation at the fourth carbon from the auxiliary with pro-R facial selectivity. This strategy provides a versatile yet controllable system for regio-, chemo-, and stereoselective oxidations at inactivated C-H bonds and demonstrates the utility of chemical auxiliaries to mediate the activity of highly promiscuous enzymes.

  DOI：

  10.1021/ja200551y

文献信息

• Methods for using therapeutic compounds containing xanthinyl
  申请人：Cell Therapeutics, Inc.

  公开号：US06043250A1

  公开（公告）日：2000-03-28

  Therapeutic compounds with at least one carboxylic acid, ester or amide-substituted side chain have the formula: CORE MOIETY --(R).sub.j wherein j is an integer from one to three. The core moiety is non-cyclic or cyclic (carbocyclic or heterocyclic). R may be selected from among hydrogen, halogen, hydroxyl, amino, substituted or unsubstituted C(.sub.1-10) alkyl, C(.sub.2-10) alkenyl, carbocyclic or heterocyclic groups and at least one R has the formula I: ##STR1## wherein: one or two p are the integer one, otherwise p is two; and n is an integer from three to twenty; R.sub.1 is selected from the group consisting of substituted and unsubstituted CH.sub.2 ; NR.sub.3, R.sub.3 being hydrogen, substituted or unsubstituted C(.sub.1-20) alkyl, C.sub.(1-20) alkoxyl, C.sub.(2-20) alkenyl or C.sub.(1-20) hydroxyalkyl, or carbocyclic or heterocyclic group; O; --CHR.sub.4 O--, R.sub.4 being substituted or unsubstituted C.sub.(1-20) alkyl, C.sub.(1-20) alkoxyl, C.sub.(2-20) alkenyl, C.sub.(1-20) hydroxyalkyl, or R.sub.2 and R.sub.4 join to form a substituted or unsubstituted heterocycle having four to seven ring atoms, the ether group --O-- of --CHR.sub.4 O-- being a member of the heterocycle. R.sub.2 is selected from the group consisting of hydrogen; halogen; substituted or unsubstituted C.sub.(1-10) alkyl; C.sub.(1-10) alkoxyl; C.sub.(2-10) alkenyl; C.sub.(1-10) hydroxyalkyl; --A(R.sub.5).sub.m, A being N or 0, m being one or two and R.sub.5 being hydrogen, a substituted or unsubstituted C.sub.(1-10) alkyl, C.sub.(1-10) alkoxyl, C.sub.(2-10) alkenyl or C.sub.(1-10) hydroxyalkyl), or carbocyclic or heterocyclic group. At least one of R.sub.1 is NR.sub.3, O or --CHR.sub.4 O--, or R.sub.2 is --A(R.sub.5).sub.m. The compounds and pharmaceutical compositions thereof are useful as therapies for diseases advanced via intracellular signaling through specific intracellular signaling pathways by mediating a signaling response to an external stimuli.

  具有至少一个羧酸、酯或酰胺取代侧链的治疗化合物具有以下公式：CORE MOIETY --(R).sub.j，其中j是从一到三的整数。核心基团是非环状或环状（碳环或杂环）。R可以从氢、卤素、羟基、氨基、取代或未取代的C(.sub.1-10)烷基、C(.sub.2-10)烯基、碳环或杂环基团中选择，至少一个R具有以下公式I：##STR1##其中：一个或两个p是整数一，否则p为二；n是从三到二十的整数；R.sub.1从取代和未取代的CH.sub.2；NR.sub.3中选择，R.sub.3为氢、取代或未取代的C(.sub.1-20)烷基、C.sub.(1-20)烷氧基、C.sub.(2-20)烯基或C.sub.(1-20)羟基烷基，或碳环或杂环基团；O；--CHR.sub.4 O--，R.sub.4为取代或未取代的C.sub.(1-20)烷基、C.sub.(1-20)烷氧基、C.sub.(2-20)烯基、C.sub.(1-20)羟基烷基，或R.sub.2和R.sub.4连接形成具有四到七个环原子的取代或未取代杂环，--CHR.sub.4 O--的醚基--O--是杂环的成员。R.sub.2从氢；卤素；取代或未取代的C.sub.(1-10)烷基；C.sub.(1-10)烷氧基；C.sub.(2-10)烯基；C.sub.(1-10)羟基烷基；--A(R.sub.5).sub.m中选择，A为N或0，m为一或二，R.sub.5为氢、取代或未取代的C.sub.(1-10)烷基、C.sub.(1-10)烷氧基、C.sub.(2-10)烯基或C.sub.(1-10)羟基烷基，或碳环或杂环基团。R.sub.1中至少有一个为NR.sub.3、O或--CHR.sub.4 O--，或R.sub.2为--A(R.sub.5).sub.m。这些化合物及其制药组合物可用作通过介导对外部刺激的信号响应来通过特定细胞内信号传导途径推进的疾病的治疗方法。
• Therapeutic compounds containing pyrimidinyl moieties
  申请人：Cell Therapeutics, Inc.

  公开号：US05807862A1

  公开（公告）日：1998-09-15

  Therapeutic compounds with at least one carboxylic acid, ester or amide-substituted side chain have the formula: CORE MOIETY--(R).sub.j wherein j is an integer from one to three. The core moiety is non-cyclic or cyclic (carbocyclic or heterocyclic). R may be selected from among hydrogen, halogen, hydroxyl, amino, substituted or unsubstituted C.sub.(1-10) alkyl, C.sub.(2-10) alkenyl, carbocyclic or heterocyclic groups and at least one R has the formula I: ##STR1## wherein: one or two p are the integer one, otherwise p is two; and n is an integer from three to twenty; R.sub.1 is selected from the group consisting of substituted and unsubstituted CH.sub.2 ; NR.sub.3, R.sub.3 being hydrogen, substituted or unsubstituted C.sub.(1-20) alkyl, C.sub.(1-20) alkoxyl, C.sub.(2-20) alkenyl or C.sub.(1-20) hydroxyalkyl, or carbocyclic or heterocyclic group; O; --CHR.sub.4 O--, R.sub.4 being substituted or unsubstituted C.sub.(1-20) alkyl, C.sub.(1-20) alkoxyl, C.sub.(2-20) alkenyl, C.sub.(1-20) hydroxyalkyl, or R.sub.2 and R.sub.4 join to form a substituted or unsubstituted heterocycle having four to seven ring atoms, the ether group --O-- of --CHR.sub.4 O-- being a member of the heterocycle. R.sub.2 is selected from the group consisting of hydrogen; halogen; substituted or unsubstituted C.sub.(1-10) alkyl; C.sub.(1-10) alkoxyl; C.sub.(2-10) alkenyl; C.sub.(1-10) hydroxyalkyl; --A(R.sub.5).sub.m, A being N or O, m being one or two and R.sub.5 being hydrogen, a substituted or unsubstituted C.sub.(1-10) alkyl, C.sub.(1-10) alkoxyl, C.sub.(2-10) alkenyl or C.sub.(1-10) hydroxyalkyl), or carbocyclic or heterocyclic group. At least one of R.sub.1 is NR.sub.3, O or --CHR.sub.4 O--, or R.sub.2 is --A(R.sub.5).sub.m. The compounds and pharmaceutical compositions thereof are useful as therapies for diseases advanced via intracellular signaling through specific intracellular signaling pathways by mediating a signaling response to an external stimuli.

  具有至少一个羧酸、酯或酰胺取代侧链的治疗化合物具有以下公式：CORE MOIETY--(R).sub.j，其中j是从一到三的整数。核心基团是非环状或环状（碳环或杂环）。R可以从氢、卤素、羟基、氨基、取代或未取代的C.sub.(1-10)烷基、C.sub.(2-10)烯基、碳环或杂环基团中选择，至少一个R具有以下公式I：##STR1##其中：一个或两个p是整数一，否则p是二；n是从三到二十的整数；R.sub.1从取代和未取代的CH.sub.2；NR.sub.3中选择，R.sub.3为氢、取代或未取代的C.sub.(1-20)烷基、C.sub.(1-20)烷氧基、C.sub.(2-20)烯基或C.sub.(1-20)羟基烷基，或碳环或杂环基团；O；--CHR.sub.4 O--，R.sub.4为取代或未取代的C.sub.(1-20)烷基、C.sub.(1-20)烷氧基、C.sub.(2-20)烯基、C.sub.(1-20)羟基烷基，或R.sub.2和R.sub.4结合形成具有四到七个环原子的取代或未取代杂环，--CHR.sub.4 O--的醚基--O--是杂环的成员。R.sub.2从氢、卤素、取代或未取代的C.sub.(1-10)烷基、C.sub.(1-10)烷氧基、C.sub.(2-10)烯基、C.sub.(1-10)羟基烷基；--A(R.sub.5).sub.m中选择，A为N或O，m为一或二，R.sub.5为氢、取代或未取代的C.sub.(1-10)烷基、C.sub.(1-10)烷氧基、C.sub.(2-10)烯基或C.sub.(1-10)羟基烷基，或碳环或杂环基团。R.sub.1中至少有一个为NR.sub.3、O或--CHR.sub.4 O--，或R.sub.2为--A(R.sub.5).sub.m。这些化合物及其制药组合物可用作通过介导对外部刺激的信号响应来通过特定细胞内信号传导途径推进的疾病的治疗方法。
• Therapeutic compounds containing xanthinyl
  申请人：Cell Therapeutics, Inc.

  公开号：US06100271A1

  公开（公告）日：2000-08-08

  Therapeutic compounds with at least one carboxylic acid, ester or amide-substituted side chain have the formula: CORE MOIETY --(R).sub.j wherein j is an integer from one to three. The core moiety is non-cyclic or cyclic (carbocyclic or heterocyclic). R may be selected from among hydrogen, halogen, hydroxyl, amino, substituted or unsubstituted C.sub.(1-10) alkyl, C.sub.(2-10) alkenyl, carbocyclic or heterocyclic groups and at least one R has the formula I: ##STR1## wherein: one or two p are the integer one, otherwise p is two; and n is an integer from three to twenty; R.sub.1 is selected from the group consisting of substituted and unsubstituted CH.sub.2 ; NR.sub.3, R.sub.3 being hydrogen, substituted or unsubstituted C.sub.(1-20) alkyl, C.sub.(1-20) alkoxyl, C.sub.(2-20) alkenyl or C.sub.(1-20) hydroxyalkyl, or carbocyclic or heterocyclic group; O; --CHR.sub.4 O--, R.sub.4 being substituted or unsubstituted C.sub.(1-20) alkyl, C.sub.(1-20) alkoxyl, C.sub.(2-20) alkenyl, C.sub.(1-20) hydroxyalkyl, or R.sub.2 and R.sub.4 join to form a substituted or unsubstituted heterocycle having four to seven ring atoms, the ether group --O-- of --CHR.sub.4 O-- being a member of the heterocycle. R.sub.2 is selected from the group consisting of hydrogen; halogen; substituted or unsubstituted C.sub.(1-10) alkyl; C.sub.(1-10) alkoxyl; C.sub.(2-10) alkenyl; C.sub.(1-10) hydroxyallyl; --A(R.sub.5).sub.m, A being N or O, m being one or two and R.sub.5 being hydrogen, a substituted or unsubstituted C.sub.(1-10) alkyl, C.sub.(1-10) alkoxyl, C.sub.(2-10) alkenyl or C.sub.(1-10) hydroxyalkyl), or carbocyclic or heterocyclic group. At least one of R.sub.1 is NR.sub.3, O or --CHR.sub.4 O--, or R.sub.2 is --A(R.sub.5).sub.m. The compounds and pharmaceutical compositions thereof are useful as therapies for diseases advanced via intracellular signaling through specific intracellular signaling pathways by mediating a signaling response to an external stimuli.

  具有至少一个羧酸、酯或酰胺取代侧链的治疗化合物具有以下公式：CORE MOIETY --(R).sub.j，其中j是从一到三的整数。核心基团是非环状或环状（碳环或杂环）。R可以从氢、卤素、羟基、氨基、取代或未取代的C.sub.(1-10)烷基、C.sub.(2-10)烯基、碳环或杂环基团中选择，至少一个R具有以下公式I：##STR1##其中：一个或两个p是整数一，否则p为二；n是从三到二十的整数；R.sub.1从取代和未取代的CH.sub.2；NR.sub.3中选择，R.sub.3为氢、取代或未取代的C.sub.(1-20)烷基、C.sub.(1-20)烷氧基、C.sub.(2-20)烯基或C.sub.(1-20)羟基烷基，或碳环或杂环基团；O；--CHR.sub.4 O--，R.sub.4为取代或未取代的C.sub.(1-20)烷基、C.sub.(1-20)烷氧基、C.sub.(2-20)烯基、C.sub.(1-20)羟基烷基，或R.sub.2和R.sub.4结合形成具有四到七个环原子的取代或未取代杂环，--CHR.sub.4 O--的醚基--O--为杂环的成员。R.sub.2从氢；卤素；取代或未取代的C.sub.(1-10)烷基；C.sub.(1-10)烷氧基；C.sub.(2-10)烯基；C.sub.(1-10)羟基烯基；--A(R.sub.5).sub.m中选择，A为N或O，m为一或二，R.sub.5为氢、取代或未取代的C.sub.(1-10)烷基、C.sub.(1-10)烷氧基、C.sub.(2-10)烯基或C.sub.(1-10)羟基烷基，或碳环或杂环基团。R.sub.1中至少有一个为NR.sub.3、O或--CHR.sub.4 O--，或R.sub.2为--A(R.sub.5).sub.m。这些化合物及其制药组合物可用作通过介导对外部刺激的信号响应来通过特定细胞内信号传导途径推进的疾病的治疗方法。
• Cell signaling inhibitors
  申请人：Cell Therapeutics, Inc.

  公开号：US05470878A1

  公开（公告）日：1995-11-28

  Therapeutic compounds have the formula: (X)j-(non-cyclic core moiety), j being an integer from one to three, the core moiety is non-cyclic and X is a racemic mixture, R or S enantiomer, solvate, hydrate, or salt of: ##STR1## *C is a chiral carbon atom, n is an integer from one to four (preferably from one to three), one or more carbon atoms of (CH.sub.2).sub.n may be substituted by a keto or hydroxy group, and m is an integer from one to fourteen. Independently, R.sub.1 and R.sub.2 may be a hydrogen, a straight or branched chain alkane or alkene of up to twelve carbon atoms in length, or --(CH.sub.2).sub.w R.sub.5, w being an integer from two to fourteen and R.sub.5 being a mono-, di- or tri-substituted or unsubstituted aryl group, substituents on R.sub.5 being hydroxy, chloro, fluoro, bromo, or C.sub.1-6 alkoxy. Or jointly, R.sub.1 and R.sub.2 form a substituted or unsubstituted, saturated or unsaturated heterocyclic group having from four to eight carbon atoms, N being a hetero atom. R.sub.3 is a hydrogen or C.sub.1-3. Or, therapeutic compounds may also have the formula: ##STR2## R.sub.4 is a hydrogen, a straight or branched chain alkane or alkene of up to eight carbon atoms in length, --(CH.sub.2).sub.w R.sub.5, w being an integer from two to fourteen and R.sub.5 being a mono-, di- or tri-substituted or unsubstituted aryl group, substituents on R.sub.5 being hydroxy, chloro, fluoro, bromo, or C.sub.1-6 alkoxy, or a substituted or unsubstituted, saturated or unsaturated heterocyclic group having from four to eight carbon atoms. r and s are independently integers from one to four, the sum (r+s) not being greater than five. t is an integer from one to fourteen and one or more carbon atoms of (CH.sub.2).sub.s or (CH.sub.2).sub.t may be substituted by a keto or hydroxy group.

  治疗性化合物的化学式为：(X)j-(非环核心基团)，其中j为1到3之间的整数，核心基团为非环状，X为一个消旋混合物、R或S对映体、溶剂化合物、水合物或盐类：*C为手性碳原子，n为1到4之间的整数（最好为1到3），(CH.sub.2).sub.n的一个或多个碳原子可被酮基或羟基取代，m为1到14之间的整数。独立地，R.sub.1和R.sub.2可以是氢、直链或支链烷烯链，长度最多为12个碳原子，或--(CH.sub.2).sub.w R.sub.5，其中w为2到14之间的整数，R.sub.5为单取代、双取代或三取代的芳基基团，R.sub.5上的取代基为羟基、氯、氟、溴或C.sub.1-6烷氧基。或者，R.sub.1和R.sub.2共同形成一个取代或未取代、饱和或不饱和的杂环基团，含有4到8个碳原子，N为杂原子。R.sub.3为氢或C.sub.1-3。或者，治疗性化合物也可以具有以下化学式：R.sub.4为氢、直链或支链烷烯链，长度最多为8个碳原子，--(CH.sub.2).sub.w R.sub.5，其中w为2到14之间的整数，R.sub.5为单取代、双取代或三取代的芳基基团，R.sub.5上的取代基为羟基、氯、氟、溴或C.sub.1-6烷氧基，或者为一个取代或未取代、饱和或不饱和的含有4到8个碳原子的杂环基团。r和s独立地为1到4之间的整数，和不大于5。t为1到14之间的整数，(CH.sub.2).sub.s或(CH.sub.2).sub.t的一个或多个碳原子可被酮基或羟基取代。
• Olefin substituted long chain compounds
  申请人：Cell Therapeutics, Inc.

  公开号：US05521315A1

  公开（公告）日：1996-05-28

  There is disclosed an olefin-substituted compound having the formula: R--(core moiety), wherein R is a straignt chain hydrocarbon having at least one double bond and a carbon chain length of from about 6 to about 18 carbon atoms, wherein multiple double bonds are separated from each other by at least three carbon atoms, wherein the closest double bond to the core moiety is at least five carbon atoms from the core moiety, and wherein the hydrocarbon chain may be substituted by a hydroxyl, halo, keto or dimethylanimo group and/or interrupted by an oxygen atom and salts thereof and pharmaceutical compositions thereof.

  公开了一种具有以下结构的烯烃取代化合物：R--（核心基团），其中R是直链碳氢化合物，具有至少一个双键，碳链长度约为6至18个碳原子，多个双键之间至少相隔三个碳原子，最接近核心基团的双键距离核心基团至少五个碳原子，碳氢链可能被羟基、卤素、酮基或二甲氨基基团取代和/或由氧原子中断，以及其盐和药物组合物。