1-(9-癸烯基)-3,7-二甲基黄嘌呤 | 156918-57-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 1-(9-癸烯基)-3,7-二甲基黄嘌呤
• 英文名称: 1-(9-Decenyl)-3,7-dimethylxanthine
• 英文别名: 1-dec-9-enyl-3,7-dimethylpurine-2,6-dione
• CAS: 156918-57-9
• 化学式: C₁₇H₂₆N₄O₂
• 分子量: 318.419
• InChiKey: KOLYQXURVMTUHF-UHFFFAOYSA-N

物化性质

• 沸点：
  507.8±52.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 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-(9-癸烯基)-3,7-二甲基黄嘌呤 、 N-甲基吗啉氧化物 在 四氧化锇 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 以93%的产率得到1-(9',10'-dihydroxydecyl)-3,7-dimethylxanthine
  参考文献：
  名称：

  Electronegative-substituted long chain xanthine compounds

  摘要：

  治疗化合物，包括已解决的对映体和/或非对映体、水合物、盐、溶剂物和其混合物，其化学式为：##STR1## 其中R.sub.0选择自氢、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、环或杂环基团，其中取代的C.sub.(1-10)烷基、C.sub.(2-10)烯基的取代基不包括卤素；n为1至16的整数；R.sub.1、R.sub.2和R.sub.3独立地选择自卤素；卤代乙酰氧基；氢；羟基；氧代；--N.dbd.C.dbd.S；--N.dbd.C.dbd.O；--0--C.tbd.N；--C.tbd.N；--N.dbd.N.dbd.N；和--C--(R.sub.5).sub.3，其中R.sub.5独立地选择自卤素或氢，至少有一个R.sub.5为卤素，至少有一个R.sub.1、R.sub.2和R.sub.3为卤素、氰基、异氰基、异硫氰基、叠氮或卤代乙酰氧基；R.sub.4为氢、C.sub.(1-6)烷基、C.sub.(1-6)烯基、环C.sub.(4-6)烷基或苯基；(CH.sub.2).sub.n --CH.sub.a --CH.sub.b --CH.sub.c中的一个或多个氢原子可以被替换为：i) 至少一个卤素原子、羟基、氧代、取代或未取代的C.sub.(1-10)烷基、C.sub.(1-10)烷氧基烷基或C.sub.(2-10)烯基；或ii) 一个或多个不饱和键；(CH.sub.2).sub.n --CH.sub.a --CH.sub.b --CH.sub.c中的任意两个相邻的碳原子可以被至少一个氧原子分隔开。这些化合物在通过抑制选择性第二信使通路治疗或预防疾病方面有用。

  公开号：

  US06020337A1
• 作为产物：
  描述：

  可可碱 、 dec-9-en-1-yl methanesulfonate 在 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 1-(9-癸烯基)-3,7-二甲基黄嘌呤
  参考文献：
  名称：

  Olefin substituted long chain compounds

  摘要：

  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。

  公开号：

  US05521315A1

文献信息

• Halogen, isothiocyanate or azide substituted xanthines
  申请人：Cell Therapeutics, Inc.

  公开号：US05670506A1

  公开（公告）日：1997-09-23

  There is disclosed a compound having the formula: ##STR1## wherein n is an integer from 5 to 9, wherein the core moiety is a heterocylic moiety wherein C.sub.a, C.sub.b, and C.sub.c are an R or S enantiomer or racemic mixture and the C.sub.a, C.sub.b, and C.sub.c carbon atoms are bonded together by a single bond, double bond, ether or ester linkages, wherein R.sub.1, R.sub.2 and R.sub.3 are independently halo, hydroxy, hydrogen, keto, isothiocyano, azide or haloacetoxy with the proviso that at least one of R.sub.1, R.sub.2 or R.sub.3 must be a halo, isothiocyano, azide or haloacetoxy group, wherein R.sub.4 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkenyl, cyclo C.sub.4-6 alkyl, or phenyl, and wherein halo refers to fluoro, chloro, bromo and iodo and salts thereof and pharmaceutical compositions thereof.

  公开了一种具有以下公式的化合物：##STR1## 其中n是5到9的整数，核心基团是杂环基团，其中C.sub.a，C.sub.b和C.sub.c是R或S对映体或混合物，C.sub.a，C.sub.b和C.sub.c碳原子由单键，双键，乙醚或酯键连接，其中R.sub.1，R.sub.2和R.sub.3独立地是卤素，羟基，氢，酮，异硫氰酸酯，叠氮化物或卤代乙酸酯，但至少有一个R.sub.1，R.sub.2或R.sub.3必须是卤素，异硫氰酸酯，叠氮化物或卤代乙酸酯基团，其中R.sub.4为氢，C.sub.1-6烷基，C.sub.1-6烯基，环C.sub.4-6烷基或苯基，其中卤素指氟，氯，溴和碘及其盐和药物组成物。
• Acetal or ketal substituted xanthine compounds
  申请人：Cell Therapeutics, Inc.

  公开号：US05440041A1

  公开（公告）日：1995-08-08

  There is disclosed compounds and pharmaceutical compositions having a xanthine core of the formula: ##STR1## wherein each of one or two R is independently ##STR2## wherein n is an integer from about 3 to about 18 forming a hydrocarbon chain, wherein the hydrocarbon chain may have one or more double bonds (preferably in a cis configuration), and may be substituted by a hydroxyl, halo or dimethylamino group and/or interrupted by an oxygen atom. The compounds lower elevated levels of unsaturated, non-arachidonate phosphatidic acid (PA) and diacylglycerol (DAG) derived from said PA within seconds of the primary stimulus and their contact with cells. The modulatory effect depends on the nature of the target cell and the stimulus applied.

  本发明涉及一种具有黄嘌呤核的化合物和制药组合物，其化学式为：##STR1## 其中一个或两个R独立地为##STR2## 其中n为约3至18的整数，形成一个碳氢链，该碳氢链可以具有一个或多个双键（优选为顺式构型），并且可以被羟基、卤素或二甲氨基基团取代和/或被氧原子中断。该化合物能够在细胞的初级刺激和它们与细胞接触的几秒钟内降低非饱和、非花生四烯酸磷脂酸（PA）和二酰基甘油（DAG）的升高水平。调节效应取决于靶细胞的性质和应用的刺激。
• Substituted long chain alcohol xanthine compounds
  申请人：Cell Therapeutics, Inc.

  公开号：US05473070A1

  公开（公告）日：1995-12-05

  There is disclosed compounds and pharmaceutical compositions comprising compounds of the formula: ##STR1## wherein each of one or two R is independently ##STR2## wherein n is an integer from 7 to 20, at least one of X or Y is --OH and if one of X or Y is --OH then the other X or Y is H, CH.sub.3, CH.sub.3 --CH.sub.2, CH.sub.3 --(CH.sub.2).sub.2 --, or (CH.sub.3).sub.2 --CH.sub.2 --, and W.sub.1, W.sub.2, and W.sub.3 is independently H, CH.sub.3, CH.sub.3 --CH.sub.2, CH.sub.3 --(CH.sub.2).sub.2 --, or (CH.sub.3).sub.2 --CH.sub.2 --, and wherein the alkyl groups may be substituted by a hydroxyl, halo or dimethylamino group and/or interrupted by an oxygen atom, H or alkyl (1-4C), including resolved enantiomers and/or diastereomers, salts and mixtures thereof. In particular, the compounds lower elevated levels of unsaturated, non-arachidonate phosphatidic acid (PA) and diacylglycerol (DAG) derived from said PA within seconds of the primary stimulus and their contact with said cells. The modulatory effect depends on the nature of the target cell and the stimulus applied.

  本发明涉及一种化合物和制药组合物，其中化合物的结构式为：##STR1## 其中的一个或两个R各自独立地为##STR2## 其中n为7到20的整数，X或Y中至少一个为--OH，如果X或Y中的一个为--OH，则另一个X或Y为H，CH.sub.3，CH.sub.3 --CH.sub.2，CH.sub.3 --(CH.sub.2).sub.2 --，或(CH.sub.3).sub.2 --CH.sub.2 --，而W.sub.1，W.sub.2和W.sub.3各自独立地为H，CH.sub.3，CH.sub.3 --CH.sub.2，CH.sub.3 --(CH.sub.2).sub.2 --，或(CH.sub.3).sub.2 --CH.sub.2 --，其中烷基基团可以被羟基，卤素或二甲氨基基团取代和/或由氧原子、H或烷基(1-4C)打断，包括分离的对映异构体和/或二面体异构体、盐和混合物。特别地，这些化合物可以在与细胞接触的几秒钟内降低非花生四烯酸磷脂酸（PA）和由该PA产生的二酰基甘油（DAG）的升高水平。调节作用取决于靶细胞的性质和施加的刺激。
• Acetal-and ketal-substituted pyrimidine compounds
  申请人：Cell Therapeutics, Inc.

  公开号：US05777115A1

  公开（公告）日：1998-07-07

  Acetal-and ketal-substituted compounds and pharmaceutical compositions thereof have the following formula: CORE MOIETY--(R).sub.j, including resolved enantiomers and/or diastereomers, hydrates, salts, solvates and mixtures thereof. j is an integer from one to three, the core moiety is non-cyclic or cyclic a monocyclic moiety having at least one nitrogen atom within the ring and R may be selected from among hydrogen, halogen, hydroxyl, amino, substituted or unsubstituted alkyl C.sub.(1-6), alkenyl C.sub.(2-6), cyclic or heterocyclic groups, and groups having a structure prescribed by formula I. At least one R has the formula I: --(CH.sub.2).sub.n --C--(R.sub.1).sub.3 I wherein n is an integer from three to twenty; R.sub.1 is selected from among hydrogen; halogen; hydroxide; substituted or unsubstituted C.sub.(1-6) alkyl, C.sub.(1-6) alkoxy, C.sub.2-6) alkenyl, cyclic or heterocyclic group; --OR.sub.2, R.sub.2 being hydrogen or a substituted or unsubstituted C.sub.(1-6) alkyl, C.sub.(2-6) alkenyl, cyclic or heterocyclic group; --(CH.sub.2).sub.p --C(R.sub.3).sub.3 (wherein p is zero or an integer from one to ten, R.sub.3 is hydrogen, halogen, hydroxide, substituted or unsubstituted C.sub.(1-6) alkyl, C.sub.(1-6) alkoxy, C.sub.(2-6) alkenyl, cyclic or heterocyclic group, or --OR.sub.2, R.sub.2 being defined above). The inventive compounds are useful in a large variety of therapeutic indications for treating or preventing disease mediated by intracellular signaling through specific intracellular signaling pathways.

  Acetal和ketal取代化合物及其制药组合物具有以下公式：CORE MOIETY--(R).sub.j，包括已解决的对映体和/或非对映体，水合物，盐，溶剂合物和它们的混合物。j是从一到三的整数，核心基团是非环或环的单环基团，环中至少有一个氮原子，R可以从氢，卤素，羟基，氨基，取代或未取代的烷基C.sub.(1-6)，烯基C.sub.(2-6)，环或杂环基团和具有公式I所规定的结构的基团中选择。至少有一个R具有公式I：--(CH.sub.2).sub.n --C--(R.sub.1).sub.3 I，其中n是从三到二十的整数；R.sub.1从氢，卤素，羟基，取代或未取代的C.sub.(1-6)烷基，C.sub.(1-6)烷氧基，C.sub.2-6)烯基，环或杂环基团中选择；--OR.sub.2，其中R.sub.2为氢或取代或未取代的C.sub.(1-6)烷基，C.sub.(2-6)烯基，环或杂环基团；--(CH.sub.2).sub.p --C(R.sub.3).sub.3（其中p为零或从一到十的整数，R.sub.3为氢，卤素，羟基，取代或未取代的C.sub.(1-6)烷基，C.sub.(1-6)烷氧基，C.sub.(2-6)烯基，环或杂环基团，或--OR.sub.2，其中R.sub.2如上定义）。创新化合物在治疗或预防通过特定细胞内信号通路介导的疾病方面具有广泛的治疗适应症。
• 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.

  至少具有一个羧酸、酯或酰胺取代侧链的治疗化合物的公式为：CORE MOIETY--(R).sub.j，其中j是从1到3的整数。核心部分是非环状或环状（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，并且至少有一个R的公式为I：##STR1## 其中：一个或两个p是整数1，否则p是2；n是从3到20的整数；R.sub.1从所选的取代和未取代的CH.sub.2；NR.sub.3，其中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，或碳环或杂环基团中选择；O；--CHR.sub.4 O--，其中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的杂环，--CHR.sub.4 O--的醚基是杂环的成员。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，其中A为N或O，m为1或2，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，或碳环或杂环基团中选择。至少有一个R.sub.1为NR.sub.3、O或--CHR.sub.4 O--，或者R.sub.2为--A(R.sub.5).sub.m。该化合物及其制药组合物可用作治疗通过介导对外部刺激的信号响应的特定细胞内信号通路而进展的疾病的疗法。