(R)-8-aminomethyl-1-(5-cyanohexyl)-3-methylxanthine | 301536-71-0

• 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: (R)-8-aminomethyl-1-(5-cyanohexyl)-3-methylxanthine
• 英文别名: (2R)-6-[8-(aminomethyl)-3-methyl-2,6-dioxo-7H-purin-1-yl]-2-methylhexanenitrile
• CAS: 301536-71-0
• 化学式: C₁₄H₂₀N₆O₂
• 分子量: 304.352
• InChiKey: YRPIQORLRGDLEJ-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  、 三氟乙酸 、 (R)-1-(5-cyanohexyl)-8-(N-BOC-aminomethyl)-3-methylxanthine 在 ammonia methanol 、 crude product 、 silica gel 、 ammonium hydroxide 、 水 、 甲醇乙酸乙酯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以to provide (R)-8-aminomethyl-1-(5-cyanohexyl)-3-methylxanthine (0.06 g, 38% yield) as a white solid的产率得到(R)-8-aminomethyl-1-(5-cyanohexyl)-3-methylxanthine
  参考文献：
  名称：

  Therapeutic compounds for inhibiting interleukin-12 signaling and methods for using same

  摘要：

  具有六元环结构融合到五元环结构的新型杂环化合物被发现可用于治疗和预防与受白细胞介素-12（“IL-12”）细胞内信号传导影响的疾病症状或表现，例如Th1细胞介导的疾病。治疗化合物，药学上可接受的衍生物（例如，解析对映体，非对映体，互变异构体，其盐和溶剂化物）或其前药，具有以下通用公式： 每个X，Y和Z独立地从C（R3），N，N（R3）和S组成的组中选择。每个R1，R2和R3被取代或未取代，并且独立地从氢，卤素，氧代，C（1-20）烷基，C（1-20）羟基烷基，C（1-20）硫代烷基，C（1-20）烷基氨基，C（1-20）烷基氨基烷基，C（1-20）氨基烷基，C（1-20）氨基烷氧基烯基，C（1-20）氨基烷氧基炔基，C（1-20）二氨基烷基，C（1-20）三氨基烷基，C（1-20）四氨基烷基，C（5-15）氨基三烷氧基氨基，C（1-20）烷基酰胺基，C（1-20）烷基酰胺基烷基，C（1-20）酰胺基烷基，C（1-20）乙酰胺基烷基，C（1-20）烯基，C（1-20）炔基，C（3-8）烷氧基，C（1-11）烷氧基烷基和C（1-20）二烷氧基烷基中独立选择。

  公开号：

  US20050049262A1

文献信息

• Therapeutic compounds for inhibiting interleukin-12 signals and method for using same
  申请人：Klein J. Peter

  公开号：US06878715B1

  公开（公告）日：2005-04-12

  Novel heterocyclic compounds having a six membered ring structure fused to a five membered ring structure are found to be useful for the treatment and prevention of symptoms or manifestations associated with disorders affected by Interleukin-12 (“IL-12”) intracellular signaling, such as, for example, Th1 cell-mediated disorders. The therapeutic compounds, pharmaceutically acceptable derivatives (e.g., resolved enantiomers, diastereomers, tautomers, salts and solvates thereof) or prodrugs thereof, have the following general formula: Each X, Y and Z are independently selected from a member of the group consisting of C(R 3 ), N, N(R 3 ) and S. Each R 1 , R 2 and R 3 is substituted or unsubstituted and is independently selected from a member of the group consisting of hydrogen, halo, oxo, C (1-20) alkyl, C (1-20) hydroxyalkyl, C (1-20) thioalkyl, C (1-20) alkylamino, C (1-20) alkylaminoalkyl, C (1-20) aminoalkyl, C (1-20) aminoalkoxyalkenyl, C (1-20) aminoalkoxyalkynyl, C (1-20) diaminoalkyl, C (1-20) triaminoalkyl, C (1-20) tetraaminoalkyl, C (5-15) aminotrialkoxyamino, C (1-20) alkylamido, C (1-20) alkylamidoalkyl, C (1-20) amidoalkyl, C (1-20) acetamidoalkyl, C (1-20) alkenyl, C (1-20) alkynyl, C (3-8) alkoxyl, C (1-11) alkoxyalkyl, and C (1-20) dialkoxyalkyl.

  具有六元环结构融合到五元环结构的新型杂环化合物被发现可用于治疗和预防受白细胞介素-12（“IL-12”）细胞内信号影响的疾病症状或表现，例如Th1细胞介导的疾病。这些治疗化合物、药物可接受的衍生物（例如，解决对映体、顺反异构体、互变异构体、盐和溶剂化物）或其前药具有以下通用式：每个X、Y和Z独立地选择自C（R3）、N、N（R3）和S的一员。每个R1、R2和R3都是取代或未取代的，且独立地选择自氢、卤素、氧代、C（1-20）烷基、C（1-20）羟基烷基、C（1-20）硫基烷基、C（1-20）烷基氨基、C（1-20）烷基氨基烷基、C（1-20）氨基烷基、C（1-20）氨基烷氧基烯基、C（1-20）氨基烷氧基炔基、C（1-20）二氨基烷基、C（1-20）三氨基烷基、C（1-20）四氨基烷基、C（5-15）氨基三烷氧基氨基、C（1-20）烷基酰胺、C（1-20）烷基酰胺烷基、C（1-20）酰胺基烷基、C（1-20）乙酰胺基烷基、C（1-20）烯基、C（1-20）炔基、C（3-8）烷氧基、C（1-11）烷氧基烷基和C（1-20）二烷氧基烷基。
• XANTHINE DERIVATIVES AND ANALOGS AS CELL SIGNALLING INHIBITORS
  申请人：CELL THERAPEUTICS, INC.

  公开号：EP1171442B1

  公开（公告）日：2005-12-07
• COMPOSITIONS AND METHODS FOR TREATING DIABETES USING LISOFYLLINE ANALOGS AND ISLET NEOGENESIS ASSOCIATED PEPTIDE
  申请人：DiaKine Therapeutics, Inc.

  公开号：US20130122050A1

  公开（公告）日：2013-05-16

  Pharmaceutical compositions and methods are provided for treating diabetes and/or restoring β-cell mass and function in a mammal in need thereof. Type 1 diabetes mellitus (T1 DM) is an autoimmune disorder characterized by immune damage to pancreatic beta-cells. Lisofylline analogs (LSF analogs) are immunomodulators that reduce interlukin 12 signaling and reduce the onset of T1 DM in non-obese diabetic (NOD) mice. A combination therapy with both LSF analog (pretreatment) and INGAP provides protection from autoimmune destruction. The concomitant or combination of an LSF analog and INGAP after pre-treatment with an LSF analog is an effective therapy for a disease or condition resulting from the loss of pancreatic islet cells or insulin production in a mammal.
• US6878715B1
  申请人：——

  公开号：US6878715B1

  公开（公告）日：2005-04-12
• [EN] XANTHINE DERIVATIVES AND ANALOGS AS CELL SIGNALING INHIBITORS<br/>[FR] DERIVES DE XANTHINE ET ANALOGUES COMME INHIBITEURS DE TRANSMISSION DES SIGNAUX INTRACELLULAIRES ET EXTRACELLULAIRES
  申请人：CELL THERAPEUTICS INC

  公开号：WO2000061583A1

  公开（公告）日：2000-10-19

  Novel heterocyclic compounds having a six membered ring structure fused to a five membered ring structure are found to be useful for the treatment and prevention of symptoms or manifestations associated with disorders affected by Interleukin-12 ('IL-12') intracellular signalling, such as, for example, Th1 cell-mediated disorders. The therapeutic compounds, pharmaceutically acceptable derivatives (e.g., resolved enantiomers, diastereomers, tautomers, salts and solvates thereof) or prodrugs thereof, have the general formula (I). Each X, Y and Z are independently selected from a member of the group consisting of C(R3), N, N(R3) and S. Each R1, R2 and R3 is substituted or unsubstituted and is independently selected from a member of the group consisting of hydrogen, halo, oxo, C(1-20)alkyl, C(1-20)hydroxyalkyl, C(1-20)thioalklyl, C(1-20)alkylamino, C(1-20)alkylaminoalkyl, C(1-20)aminoalkyl, C(1-20)aminoalkoxyalkenyl, C(1-20)aminoalkoxyalkynyl, C(1-20)diaminoalkyl, C(1-20)triaminoalkyl, C(1-20)tetraaminoalkyl, C(5-15)aminotrialkoxyamino, C(1-20)alkylamido, C(1-20)alkylamidoalkyl, C(1-20)amidoalkyl, C(1-20)acetamidoalkyl, C(1-20)alkenyl, C(1-20)alkynyl, C(3-8)alkoxyl, C(1-11)alkoxyalkyl, and C(1-20)dialkoxyalkyl.