3',5'-dichloro-2,6-dimethoxybiphenyl-4-carbaldehyde | 1055351-98-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3',5'-dichloro-2,6-dimethoxybiphenyl-4-carbaldehyde
• 英文别名: 4-(3,5-Dichlorophenyl)-3,5-dimethoxybenzaldehyde；4-(3,5-dichlorophenyl)-3,5-dimethoxybenzaldehyde
• CAS: 1055351-98-8
• 化学式: C₁₅H₁₂Cl₂O₃
• 分子量: 311.164
• InChiKey: ZSMWGFGAUIBRFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3',5'-dichloro-2,6-dimethoxybiphenyl-4-carbaldehyde 在 magnesium 、 1,2-二溴乙烷 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 (4-butylphenyl)(3',5'-dichloro-2,6-dimethoxybiphenyl-4-yl)methanone
  参考文献：
  名称：

  Synthesis and biological evaluation of (3′,5′-dichloro-2,6-dihydroxy-biphenyl-4-yl)-aryl/alkyl-methanone selective CB2 inverse agonist

  摘要：

  Cannabinoid receptor 2 (CB2) selective agonists and inverse agonists possess significant potential as therapeutic agents for regulating inflammation and immune function. Although CB2 agonists have received the greatest attention, it is emerging that inverse agonists also manifest anti-inflammatory activity. In process of designing new cannabinoid ligands we discovered that the 2,6-dihydroxy-biphenyl-aryl methanone scaffold imparts inverse agonist activity at CB2 receptor without functional activity at CB1. To further explore the scaffold we synthesized a series of (3',5'-dichloro-2,6-dihydroxy-biphenyl-4-yl)-aryl/alkyl-methanone analogs and evaluated the CB1 and CB2 affinity, potency, and efficacy. The studies reveal that an aromatic C ring is required for inverse agonist activity and that substitution at the 4 position is optimum. The resorcinol moiety is required for optimum CB2 inverse agonist activity and selectivity. Antagonist studies against CP 55,940 demonstrate that the compounds 41 and 45 are noncompetitive antagonists at CB2. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.057
• 作为产物：
  描述：

  trifluoromethanesulfonic acid 4-formyl-2,6-dimethoxyphenyl ester 、 3,5-二氯苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 、 lithium chloride 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以69%的产率得到3',5'-dichloro-2,6-dimethoxybiphenyl-4-carbaldehyde
  参考文献：
  名称：

  大麻素2型受体的新型碳11标记的三芳基配体的放射性合成

  摘要：

  具有两个对大麻素亚型2（CB2）受体具有强大体外结合亲和力的新型三芳基配体2和5用发射正电子的放射性核素11 C标记。放射性配体[ 11 C] 2，[ 11 C] 5及其它们通过[ 11 C] CH 3 I对相应的苯酚前体进行O- [ 11 C]甲基化，合成了类似物[ 11 C] 3和[ 11 C] 4。 [ 11 C] 2 – 5 在老鼠的大脑中具有相对较高的摄取（> 1.2％注射剂量/ g组织）。

  DOI：

  10.1016/j.bmcl.2010.01.074

文献信息

• Tri-aryl/heteroaromatic cannabinoids and use thereof
  申请人：Moore Bob M.

  公开号：US20080234293A1

  公开（公告）日：2008-09-25

  Cannabinoid derivatives according to formula (I) are disclosed wherein, X, Y, R 1 , R 2 , and W can have the definitions provided herein. Without limitation, use of such compounds, their salts or pro-drug, or compositions containing the compounds, salts, or pro-drug, to modify the activity of CB1 and CB2 receptors and treat conditions mediated by these receptors.

  根据公式（I）披露了大麻素衍生物，其中，X、Y、R1、R2和W可以具有此处提供的定义。无限制地使用这些化合物、它们的盐或前药，或含有这些化合物、盐或前药的组合物，以修改CB1和CB2受体的活性，并治疗由这些受体介导的疾病。
• Tri-Aryl/Heteroaromatic Cannabinoids and Use Thereof
  申请人：Moore, II Bob M.

  公开号：US20110207748A1

  公开（公告）日：2011-08-25

  Cannabinoid derivatives according to formula (I) are disclosed wherein, X, Y, R 1 , R 2 , and W can have the definitions provided herein. Without limitation, use of such compounds, their salts or pro-drug, or compositions containing the compounds, salts, or pro-drug, to modify the activity of CB1 and CB2 receptors and treat conditions mediated by these receptors.

  公开了公式（I）所示的大麻素衍生物，其中X，Y，R1，R2和W可以具有此处提供的定义。无限制地使用这些化合物，它们的盐或前药，或含有这些化合物，盐或前药的组合物，以修改CB1和CB2受体的活性并治疗由这些受体介导的疾病。
• Design and synthesis of novel tri-aryl CB2 selective cannabinoid ligands
  作者：Himanshu Bhattacharjee、Steven N. Gurley、Bob M. Moore

  DOI：10.1016/j.bmcl.2009.01.100

  日期：2009.3

  A novel series of cannabinoid ligands with a structurally unique tri-aryl core has been designed, synthesized and assayed. Receptor binding assays show that these compounds possess CB2 receptor sub-type selectivity with binding affinities ranging from 1.07 (+/-0.05) for 7 to 4.77 (+/-0.57) nM for 6. The selectivity of the compounds was enhanced 9-600-fold for the CB2 receptor over the CB1 receptor. The results of our present study identify a novel, highly selective cannabinoid scaffold with a non-classical core. (C) 2009 Elsevier Ltd. All rights reserved.
• EP2131655B1
  申请人：——

  公开号：EP2131655B1

  公开（公告）日：2014-05-07
• TRI-ARYL/HETEROAROMATIC CANNABINOIDS AND USE THEREOF
  申请人：The University of Tennessee Research Foundation

  公开号：EP2131655A2

  公开（公告）日：2009-12-16