1-(6-hydroxy-hexyl)-3,7-dimethyl-3,7-dihydro-purine-2,6-dione | 56395-71-2

• 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-(6-hydroxy-hexyl)-3,7-dimethyl-3,7-dihydro-purine-2,6-dione
• 英文别名: 1-(6-hydroxyhexyl)-3,7-dimethylxanthine；1-(6-Hydroxyhexyl)-3,7-dimethyl-xanthin；1-(6-hydroxyhexyl)-3,7-dimethylpurine-2,6-dione
• CAS: 56395-71-2
• 化学式: C₁₃H₂₀N₄O₃
• 分子量: 280.327
• InChiKey: FQMLNCMGNMEXAL-UHFFFAOYSA-N

物化性质

• 沸点：
  518.3±56.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  78.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(6-hydroxy-hexyl)-3,7-dimethyl-3,7-dihydro-purine-2,6-dione 在 三苯基膦 作用下， 以 四氯化碳 为溶剂， 以53%的产率得到1-(6-chlorohexyl)3,7-dimethylxanthine
  参考文献：
  名称：

  Halogen, isothiocyanate or azide substituted xanthines

  摘要：

  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。

  公开号：

  US05670506A1
• 作为产物：
  描述：

  可可碱 以90%的产率得到1-(6-hydroxy-hexyl)-3,7-dimethyl-3,7-dihydro-purine-2,6-dione
  参考文献：
  名称：

  Pharmaceutical compositions

  摘要：

  一种药物组合物，其主要成分为公式##STR1##中的化合物，其中R.sub.1、R.sub.2和R.sub.3中的一个是具有5至8个碳原子的ω-或(ω-1)-羟基烷基基团，羟基团至少与黄嘌呤核之间相隔2个碳原子，基团R.sub.1和R.sub.3不是羟基烷基基团，则为氢或甲基，可以相同也可以不同，而R.sub.2是所述的羟基烷基基团或甲基，化合物的公式为(I)，以及用于治疗涉及脑血流不足疾病的药物产品。

  公开号：

  US04515795A1

文献信息

• Electronegative-substituted long chain xanthine compounds
  申请人：Cell Therapeutics, Inc.

  公开号：US06020337A1

  公开（公告）日：2000-02-01

  Therapeutic compounds, including resolved enantiomers and/or diastereomers, hydrates, salts, solvates and mixtures thereof, having a formula: ##STR1## wherein R.sub.0 is selected from the group consisting of hydrogen, halo, hydroxyl, amino, substituted or unsubstituted C.sub.(1-10) alkyl, C.sub.(2-10) alkenyl, cyclic or heterocyclic groups, wherein the substituents of substituted C.sub.(1-10) alkyl, C.sub.(2-10) alkenyl are other than halo; n is an integer from one to sixteen; R.sub.1, R.sub.2, and R.sub.3 are independently selected from the group consisting of a halo; haloacetoxy; hydrogen; hydroxy; oxo; --N.dbd.C.dbd.S; --N.dbd.C.dbd.O; --0--C.tbd.N; --C.tbd.N; --N.dbd.N.dbd.N; and --C--(R.sub.5).sub.3, R.sub.5 being independently a halo or hydrogen, at least one R.sub.5 being halo, at least one of R.sub.1, R.sub.2, and R.sub.3 being halo, cyano, isocyano, isothiocyano, azide or haloacetoxy group; R.sub.4 is hydrogen, C.sub.(1-6) alkyl, C.sub.(1-6) alkenyl, cyclo C.sub.(4-6) alkyl, or phenyl; one or more hydrogen atoms of (CH.sub.2).sub.n --CH.sub.a --CH.sub.b --CH.sub.c may be replaced with: i) at least one of halogen atom, hydroxyl, oxo, substituted or unsubstituted C.sub.(1-10) alkyl, C.sub.(1-10) alkoxyalkyl, or C.sub.(2-10) alkenyl; or ii) one or more unsaturated bonds; and any two adjacent carbon atoms of (CH.sub.2).sub.n --CH.sub.a --CH.sub.b --CH.sub.c may be instead separated by at least one oxygen atom. These compounds are useful in treating or preventing diseases by inhibiting selective second messenger pathways.

  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。
• LISOFYLLINE ANALOGS AND METHODS FOR USE
  申请人：Macdonald Timothy L.

  公开号：US20100105690A1

  公开（公告）日：2010-04-29

  Analogs of a Lisofylline (LSF), and synthetic methods for the preparation of such analogs are provided. The analogs of LSF provided have the ability to protect cell viability, particularly the ability to protect pancreatic β-cells.

  提供了Lisofylline（LSF）的类似物以及制备这些类似物的合成方法。所提供的LSF类似物具有保护细胞存活能力，特别是保护胰岛β细胞的能力。
• Amine substituted compounds
  申请人：Cell Therapeutics, Inc.

  公开号：US05801182A1

  公开（公告）日：1998-09-01

  Compounds and pharmaceutical compositions, including resolved enantiomers and/or diastereomers, hydrates, salts, solvates and mixtures thereof, have the formula: CORE MOIETY --(R).sub.j In these compounds, j is an integer from one to three; the core moiety is a cyclic core, the cyclic core being non-cyclic or at least one five- to seven-member non-heterocyclic ring or heterocycle; and R is selected from the group consisting of amine, hydrogen, halogen, hydroxyl, substituted or unsubstituted C.sub.(1-10) alkyl, C.sub.(2-10) alkenyl, cyclic or heterocyclic group or formula I. At least one R having formula I: ##STR1## In formula I, n is an integer from four to twenty; and each R.sub.1 or R.sub.2 is independently hydrogen, substituted or unsubstituted C.sub.(1-20) alkyl, C.sub.(1-20) alkoxyl, C.sub.(2-20) alkenyl or cyclic or heterocyclic group. The compounds are useful in treating or preventing, for example, sepsis syndrome, hematopoietic or organ toxicity, cancer, viral activity, AIDS and AIDS-related indications, allopecia caused by cytotoxic therapies, and progression of an inflammatory or autoimmune disease.

  化合物和制药组合物，包括已解决的对映体和/或非对映异构体、水合物、盐、溶剂化物和它们的混合物，其化学式为：CORE MOIETY --(R).sub.j 在这些化合物中，j 是一个从一到三的整数；核心基团是一个环状核心，该环状核心是非环状的或至少包含一个五至七元非杂环或杂环；而R是从胺、氢、卤素、羟基、取代或未取代的C.sub.(1-10)烷基、C.sub.(2-10)烯基、环状或杂环基团或式I的基团中选择的。至少有一个具有式I的R：##STR1## 在式I中，n是一个从四到二十的整数；每个R.sub.1或R.sub.2都是独立的氢、取代或未取代的C.sub.(1-20)烷基、C.sub.(1-20)烷氧基、C.sub.(2-20)烯基或环状或杂环基团。这些化合物在治疗或预防败血症综合症、造血或器官毒性、癌症、病毒活性、艾滋病和艾滋病相关症状、由细胞毒性治疗引起的脱发以及炎症或自身免疫性疾病的进展方面是有用的。
• 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。
• Amine substituted xanthinyl compounds
  申请人：Cell Therapeutics, Inc.

  公开号：US05807861A1

  公开（公告）日：1998-09-15

  A method for treating a disease caused by an undesirable cell response mediated by a proliferative intracellular signaling pathway is provided wherein an effective amount of a compound is administered. The compound, resolved enantiomers, diastereomers, hydrates, salts, solvates and mixtures thereof, has the formula CORE MOIETY--(R).sub.j wherein j is an integer from one to three; the core moiety is xanthinyl; and R is independently selected from the group consisting of amine, hydrogen, halogen, hydroxyl, C.sub.(1-10) alkyl, C.sub.(2-10) alkenyl, 2-bromopropyl, 4-chloropentyl, cyclohexyl, cyclopentyl, 3-dimethylaminobutyl, 2-hydroxyethyl, 5-hydroxyhexyl, 3-hydroxy-n-butyl, 3-hydroxypropyl, 2-methoxyethyl, 4-methoxy-n-butyl, phenyl, and formula I, at least one R comprising formula I ##STR1## wherein (CH.sub.2).sub.n is optionally substituted; n is an integer from five to twenty; each R.sub.1 or R.sub.2 is independently hydrogen or an optionally substituted group that is herein defined; and wherein, when the (CH.sub.2).sub.n, R.sub.1 or R.sub.2 is substituted, a substituent is selected from the group consisting of carbamoyl, primary, secondary and tertiary amino, C.sub.(2-8) alkenyl, C.sub.(1-8) alkyl, C.sub.(1-8) alkoxyl, C.sub.(1-8) hydroxyalkyl, azido, carbonato, carbonyl, carboxyl, cyano, C.sub.(1-8) haloalkyl, isocyano, isomercaptocyano, phospho, phosphonato, sulfonato, alkylsulfonyl, alkylsulfoxidyl, mercaptocarbonyl, mercaptocarbonato, thioureido and ureido.

  提供了一种治疗由增殖性细胞内信号通路介导的不良细胞反应引起的疾病的方法，其中给予有效量的化合物。该化合物，包括分离的对映体、非对映体异构体、水合物、盐、溶剂化物和其混合物，具有以下公式：CORE MOIETY--(R).sub.j，其中j为1至3的整数；核心基团为黄嘌呤基团；R独立地选自以下组中的一种：胺、氢、卤素、羟基、C.sub.(1-10)烷基、C.sub.(2-10)烯基、2-溴丙基、4-氯戊基、环己基、环戊基、3-二甲氨基丁基、2-羟乙基、5-羟基己基、3-羟基正丁基、3-羟丙基、2-甲氧基乙基、4-甲氧基正丁基、苯基和公式I，其中至少一个R包括公式I，其中(CH.sub.2).sub.n是可选的取代基；n为5至20的整数；每个R.sub.1或R.sub.2独立地为氢或在此处定义的可选取代基；当(CH.sub.2).sub.n、R.sub.1或R.sub.2被取代时，取代基从以下组中选择：氨基甲酰基、一级、二级和三级氨基、C.sub.(2-8)烯基、C.sub.(1-8)烷基、C.sub.(1-8)烷氧基、C.sub.(1-8)羟基烷基、偶氮基、碳酸酯基、羰基、羧基、氰基、C.sub.(1-8)卤代烷基、异氰基、异硫氰酸酯基、磷酸基、膦酸酯基、磺酸基、烷基磺酰基、烷基亚砜基、巯基羰基、巯基碳酸酯基、硫脲基和脲基。