1-((1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)-N-methylmethanamine | 1413776-12-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-((1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)-N-methylmethanamine
• 英文别名: 1-[(1S,2R,5S)-6,6-dimethyl-2-bicyclo[3.1.1]heptanyl]-N-methylmethanamine
• CAS: 1413776-12-1
• 化学式: C₁₁H₂₁N
• 分子量: 167.294
• InChiKey: FIRNORACHPUOFJ-GUBZILKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-((1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)-N-methylmethanamine 、 2'-iodo-[1,1'-biphenyl]-4-carbaldehyde 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.5h， 以75%的产率得到1-((1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)-N-((2'-iodobiphenyl-4-yl)methyl)-N-methylmethanamine
  参考文献：
  名称：

  Chemical Subtleties in Small-Molecule Modulation of Peptide Receptor Function: The Case of CXCR3 Biaryl-Type Ligands

  摘要：

  The G protein-coupled chemokine receptor CXCR3 plays a role in numerous inflammatory events. The endogenous ligands for the chemokine receptors are peptides, but in this study we disclose small-molecule ligands that are able to activate CXCR3. A class of biaryl-type compounds that is assembled by convenient synthetic routes is described as a new class of CXCR3 agonists. Intriguingly, structure-activity relationship and structure-function relationship studies reveal that subtle chemical modifications on the outer aryl ring (e.g., either the size or position of a halogen atom) result in a full spectrum of agonist efficacies on CXCR3. Quantum mechanics calculations and nuclear Overhauser effect spectroscopy NMR studies suggest that the biaryl dihedral angle and the electronic nature of ortho-substituents play an important role in determining agonist efficacies. Compounds 38 (VUF11222) and 39 (VUF11418) are the first reported nonpeptidomimetic agonists on CXCR3, rendering them highly useful chemical tools for detailed assessment of CXCR3 activation as well as for studying downstream CXCR3 signaling.

  DOI：

  10.1021/jm301240t
• 作为产物：
  描述：

  1-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-N-methylmethanamine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 23.0h， 生成 1-((1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)-N-methylmethanamine
  参考文献：
  名称：

  Chemical Subtleties in Small-Molecule Modulation of Peptide Receptor Function: The Case of CXCR3 Biaryl-Type Ligands

  摘要：

  The G protein-coupled chemokine receptor CXCR3 plays a role in numerous inflammatory events. The endogenous ligands for the chemokine receptors are peptides, but in this study we disclose small-molecule ligands that are able to activate CXCR3. A class of biaryl-type compounds that is assembled by convenient synthetic routes is described as a new class of CXCR3 agonists. Intriguingly, structure-activity relationship and structure-function relationship studies reveal that subtle chemical modifications on the outer aryl ring (e.g., either the size or position of a halogen atom) result in a full spectrum of agonist efficacies on CXCR3. Quantum mechanics calculations and nuclear Overhauser effect spectroscopy NMR studies suggest that the biaryl dihedral angle and the electronic nature of ortho-substituents play an important role in determining agonist efficacies. Compounds 38 (VUF11222) and 39 (VUF11418) are the first reported nonpeptidomimetic agonists on CXCR3, rendering them highly useful chemical tools for detailed assessment of CXCR3 activation as well as for studying downstream CXCR3 signaling.

  DOI：

  10.1021/jm301240t

文献信息

• PYRIMIDINE COMPOUND
  申请人：Matsushima Yuji

  公开号：US20110053912A1

  公开（公告）日：2011-03-03

  A novel and excellent method for preventing and/or treating diseases related to a cannabinoid type 2 receptor, based on an agonistic action on a cannabinoid type 2 receptor. It was found that a hetero ring derivative mainly having two substituents, for example, a pyrimidine-5-carboxamide derivative having a substituent amino group at the 2-position, exhibits a potent agonistic action on a cannabinoid type 2 receptor, and can be an agent for preventing and/or treating diseases related to a cannabinoid type 2 receptor such as inflammatory diseases, pain, and the like.

  一种预防和/或治疗与大麻素2型受体相关疾病的新颖优秀方法，基于对大麻素2型受体的激动作用。发现一种异核环衍生物主要具有两个取代基，例如，在2-位置具有取代基氨基的嘧啶-5-羧酰胺衍生物，表现出对大麻素2型受体的强效激动作用，可以成为预防和/或治疗与大麻素2型受体相关疾病，如炎症性疾病、疼痛等的药物。
• [EN] COMBINATIONS COMPRISING BIPHENYL DERIVATIVES FOR USE IN THE TREATMENT OF HCV<br/>[FR] ASSOCIATIONS COMPRENANT DES DÉRIVÉS DE BIPHÉNYLE DESTINÉES À ÊTRE UTILISÉES POUR LE TRAITEMENT DU VIRUS DE L'HÉPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2015009744A1

  公开（公告）日：2015-01-22

  The present disclosure is generally directed to antiviral compounds, and more specifically directed to combinations of compounds which can inhibit the function of the NS5A protein encoded by Hepatitis C virus (HCV), compositions comprising such combinations, and methods for inhibiting the function of the NS5A protein.

  本公开涉及抗病毒化合物，更具体地涉及能够抑制由丙型肝炎病毒（HCV）编码的NS5A蛋白质的功能的化合物组合、包含这样的组合物的组合物以及抑制NS5A蛋白质功能的方法。
• Novel Biaromatic Compounds, Inhibitors of the P2X7-Receptor
  申请人：Thompson Toby

  公开号：US20080146612A1

  公开（公告）日：2008-06-19

  The invention provides compounds of formula (I), or a pharmaceutically acceptable salt thereof, wherein Ar 1 represents a group (II), (III), (IV) or (V), and A, Ar 2 , n, R 1 , R 2 , R 3 , R 4 and R 5 are as defined in the specification; a process for their preparation; pharmaceutical compositions containing them; and their use in therapy.

  该发明提供了公式（I）的化合物或其药学上可接受的盐，其中Ar1代表（II），（III），（IV）或（V）中的一个基团，而A，Ar2，n，R1，R2，R3，R4和R5如说明书中所定义；其制备过程；包含它们的制药组合物；以及它们在治疗中的应用。
• PHARMACEUTICAL COMPOSITIONS AND METHODS FOR RESTORING BETA-CELL MASS AND FUNCTION
  申请人：NADLER Jerry L.

  公开号：US20080300189A1

  公开（公告）日：2008-12-04

  Pharmaceutical compositions and methods for using are provided for restoring β-cell mass and function in a mammal in need thereof. The pharmaceutical compositions have a biological response modifier and a β-cell growth factor in admixture with a pharmaceutically acceptable carrier, adjuvant or vehicle.
• ENCAPSULATION SYSTEM
  申请人：Nadler Jerry L.

  公开号：US20090269313A1

  公开（公告）日：2009-10-29

  An encapsulation system for use in the treatment of diabetes (Types 1 or 2, and LADA) are provided. The system has (1) a delivery vehicle comprising a selectively permeable membrane that allows passage of glucose, insulin and other nutrients through the membrane, but prevents large molecules such as antibodies or inflammatory cells from passing through the membrane; (2) a population of islet cells or insulin producing cells encapsulated by said membrane; and (3) a biological response modifier that may be in contact with the membrane or encapsulated by the membrane. Generally, the biological response modifier is a compound, including resolved enantiomers, diastereomers, tautomers, salts and solvates thereof, having the following formula: wherein: X, Y and Z are independently selected from a member of the group consisting of C(R 3 ), N, N(R 3 ) and S; R 1 is selected from a member of the group consisting of hydrogen, methyl, C (5-9) alkyl, C (5-9) alkenyl, C (5-9) alkynyl, C (5-9) hydroxyalkyl, C (3-8) alkoxyl, C (5-9) alkoxyalkyl, the R 1 being optionally substituted; R 2 and R 3 are 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.