1-(5,6-oxidohexyl)-3,7-dimethylxanthine | 154719-57-0

• 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-(5,6-oxidohexyl)-3,7-dimethylxanthine
• 英文别名: 3,7-Dimethyl-1-[4-(oxiran-2-yl)butyl]purine-2,6-dione
• CAS: 154719-57-0
• 化学式: C₁₃H₁₈N₄O₃
• 分子量: 278.311
• InChiKey: MBKLDTNJXKWOCK-UHFFFAOYSA-N

物化性质

• 沸点：
  502.0±46.0 °C(Predicted)
• 密度：
  1.44±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：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  71
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(5,6-oxidohexyl)-3,7-dimethylxanthine 以 水 、 丙酮 为溶剂， 以53%的产率得到1-(6-azido-5-hydroxyhexyl)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：

  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

文献信息

• 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。
• 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。
• Substituted amino alcohol compounds
  申请人：Cell Therapeutics, Inc.

  公开号：US05641783A1

  公开（公告）日：1997-06-24

  Disclosed are compounds having a straight or branched aliphatic hydrocarbon structure of formula I: ##STR1## In formula I, n is an integer from one to four and m is an integer from four to twenty. Independently, R.sub.1 and R.sub.2 are hydrogen, a straight or branched chain alkyl, alkenyl or alkynyl of up to twenty carbon atoms in length or --(CH.sub.2).sub.w R.sub.5. If R.sub.1 or R.sub.2 is --(CH.sub.2).sub.w R.sub.5, w may be an integer from one to twenty and R.sub.5 may be an hydroxyl, halo, C.sub.1-8 alkoxyl group or a substituted or unsubstituted carbocycle or heterocycle. Alternatively, R.sub.1 and R.sub.2 may jointly form a substituted or unsubstituted, saturated or unsaturated heterocycle having from four to eight carbon atoms, N being a hetero atom of the resulting heterocycle. R.sub.3 may be either hydrogen or C.sub.1-3. In the compounds, a total sum of carbon atoms comprising R.sub.1 or R.sub.2, (CH.sub.2).sub.n and (CH.sub.2).sub.m does not exceed forty. R.sub.4 is a terminal moiety comprising a substituted or unsubstituted, oxidized or reduced ring system, the ring system having a single ring or two to three fused rings, a ring comprising from three to seven ring atoms. The disclosed compounds are effective agents to inhibit undesirable responses to cell stimuli.

  本文揭示了具有公式I的直链或支链脂肪烃结构的化合物：##STR1## 在公式I中，n是一个从一到四的整数，m是一个从四到二十的整数。独立地，R.sub.1和R.sub.2是氢，长度最多为二十个碳原子的直链或支链烷基，烯基或炔基，或者是--(CH.sub.2).sub.w R.sub.5。如果R.sub.1或R.sub.2是--(CH.sub.2).sub.w R.sub.5，w可以是一个从一到二十的整数，R.sub.5可以是一个羟基，卤素，C.sub.1-8烷氧基团或一个取代或未取代的碳环或杂环。另外，R.sub.1和R.sub.2可以共同形成一个取代或未取代的，饱和或不饱和的，由四到八个碳原子组成的杂环，N是所得杂环的杂原子。R.sub.3可以是氢或C.sub.1-3。在化合物中，包括R.sub.1或R.sub.2，(CH.sub.2).sub.n和(CH.sub.2).sub.m的碳原子总和不超过四十。R.sub.4是一个末端基团，包括一个取代或未取代的，氧化或还原的环系统，该环系统具有单环或两到三个融合环，一个环包含三到七个环原子。所述化合物是有效的抑制细胞刺激引起的不良反应的药剂。
• Amino-alcohol substituted cyclic compounds
  申请人：Cell Therapeutics, Inc.

  公开号：US05837703A1

  公开（公告）日：1998-11-17

  Therapeutic compounds have the formula: (X)j-(core moiety), j being an integer from one to three, the core moiety comprising a core moiety, the core moiety being a heterocycle having one ring or two-fused rings, each ring having five or six ring atoms, A being a carbon atom of the core moiety and attached to a terminal carbon atom of (CH.sub.2).sub.m, and X has a structure and X being 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 alkyl or alkenyl 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 alkoxyl. 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 alkyl or alkenyl 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 alkoxyl, 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 hydroxyl group.

  治疗化合物的公式为：(X)j-(核心基团)，其中j为从一到三的整数，核心基团包括一个杂环，该杂环具有一个环或两个融合的环，每个环有五个或六个环原子，A是核心基团的碳原子，连接到(CH.sub.2).sub.m的末端碳原子，而X具有结构，X是一个外消旋体混合物，R或S对映体，溶剂化物，水合物或盐，其结构如下：##STR1## *C是一个手性碳原子，n是从一到四的整数（最好从一到三），(CH.sub.2).sub.n中的一个或多个碳原子可能被酮基或羟基取代，m是从一到十四的整数。独立地，R.sub.1和R.sub.2可以是氢，长度为最多十二个碳原子的直链或支链烷基或烯基，或--(CH.sub.2).sub.w R.sub.5，其中w是从二到十四的整数，R.sub.5是一个单取代，二取代或三取代或未取代的芳基，R.sub.5上的取代基是羟基，氯，氟，溴或C.sub.1-6烷氧基。或共同地，R.sub.1和R.sub.2形成一个取代或未取代的，饱和或不饱和的杂环基团，其碳原子数为四到八，N是一个杂原子。R.sub.3是氢或C.sub.1-3。或者，治疗化合物也可以具有以下公式：##STR2## R.sub.4是氢，长度为最多八个碳原子的直链或支链烷基或烯基，--(CH.sub.2).sub.w R.sub.5，其中w是从二到十四的整数，R.sub.5是一个单取代，二取代或三取代或未取代的芳基，R.sub.5上的取代基是羟基，氯，氟，溴或C.sub.1-6烷氧基，或一个取代或未取代的，饱和或不饱和的杂环基团，其碳原子数为四到八，r和s是独立的从一到四的整数，其和（r+s）不大于五。t是从一到十四的整数，(CH.sub.2).sub.s或(CH.sub.2).sub.t中的一个或多个碳原子可能被酮基或羟基取代。
• NOVEL EPOXIDE-CONTAINING COMPOUNDS
  申请人：CELL THERAPEUTICS, INC.

  公开号：EP0662834A1

  公开（公告）日：1995-07-19