3,4-dihydro-7-methoxy-1-naphthalenecarboxylic acid | 132452-55-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,4-dihydro-7-methoxy-1-naphthalenecarboxylic acid
• 英文别名: 7-methoxy-3,4-dihydro-[1]naphthoic acid；7-Methoxy-3,4-dihydro-[1]naphthoesaeure；7-methoxy-3,4-dihydronaphthalen-1-yl-carboxylic acid；7-methoxy-3,4-dihydronaphthalene-1-carboxylic acid
• CAS: 132452-55-2
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: ROSZDWNARIOXOW-UHFFFAOYSA-N

物化性质

• 沸点：
  350.0±42.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-7-methoxy-1-naphthalenecarboxylic acid 在 氢溴酸 、 sulfur 、 溶剂黄146 作用下， 生成 7-羟基-1-萘羧酸
  参考文献：
  名称：

  The Synthesis of Phenanthrene and Hydrophenanthrene Derivatives. V. The Addition of Dienes to Cyclic α,β-Unsaturated Esters

  摘要：

  DOI：

  10.1021/ja01302a069
• 作为产物：
  描述：

  7-甲氧基-1-萘满酮 在 盐酸 、 sodium hydroxide 、 硫酸 、 2-甲基苯磺酸 、 zinc(II) iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 116.0h， 生成 3,4-dihydro-7-methoxy-1-naphthalenecarboxylic acid
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of 4a-phenanthrenamine derivatives acting at the phencyclidine binding site of the N-methyl-D-aspartate receptor complex

  摘要：

  A novel series of octahydrophenanthrenamines and their heterocyclic analogues have been synthesized as potential noncompetitive antagonists of the N-methyl-D-aspartate (NMDA) receptor complex. The compounds were evaluated for their affinity at the phencyclidine (PCP) binding site by determining their ability to displace [H-3]TCP from crude rat brain synaptic membranes. A wide range of affinities were observed, with the most potent analogs possessing IC50's equivalent to that of the reference agent MK-801 (3,dizocilpine). NMDA antagonist activity was demonstrated by prevention of glutamate-induced accumulation of [Ca-45(2+)] in cultured rat cortical neurons. Selected compounds were also studied in vivo to determine their ability to prevent the lethal effects of systemically injected NMDA in the mouse. In general, the SAR of the phenanthrenamine series may be summarized as follows: (a) for the amino group at C4a, NHMe > NH2 > NHEt much-greater-than NC5H10; (b) for the B-ring substitution, X = CH2 > S > 0; (c) unsaturation of the C ring decreases receptor affinity; (d) cis-ring fusion between the B and C rings is desirable; (e) 6-hydroxy or 6-methoxy substitution of the phenanthrenamine system identified an additional hydrogen bonding interaction that substantially increased receptor affinity; (f) spiro analogues (such as 55, IC50 = 3400 nM), which altered the point of attachment of the C ring, caused a substantial reduction in PCP-site affinity. Molecules from this series were useful for refining a pharmacophore model consistent with previous models of the PCP site. In this model, the (R)-(+)-phenanthrenamine 13 superimposes closely onto MK-801 (3), and the angular 4a-amino group is believed to hydrogen bond with a putative receptor site atom. In the phenanthrenamine and thiaphenanthrenamine series, the (R)-(+)-enantiomers (9, 13, and 44) are more potent by approximately 5-10-fold than their corresponding (S)-(-)-enantiomers with respect to their affinity for the PCP site, their ability to prevent accumulation of [Ca-45(2+)] in cultured neuronal cells, and their protection against the lethal effects of NMDA in mice. In general, there was no separation between the dose that prevented NMDA lethality and the dose that produced ataxia in mice, except in the case of the thiaphenanthrenamines 41 and 43. We have not yet obtained evidence that this small separation in activity offers a therapeutic advantage in the treatment of cerebral ischemia or other neurodegenerative disorders.

  DOI：

  10.1021/jm00066a007

文献信息

• CB2-selective cannabinoid analogues
  申请人：Martin R. Billy

  公开号：US20050009903A1

  公开（公告）日：2005-01-13

  Cannabinoid analogues that exhibit specificity for the CB 2 cannabinoid receptor are provided. The analogues are 1-methoxy-, 1-deoxy-11-hydroxy- and 11-hydroxy-1-methoxy-Δ 8 -tetrahydrocannabinols and 1-alkyl-3(1-naphthoyl)indoles. The compounds are useful for the treatment of pain (especially pain resulting from inflammation) and cancer (especially glioma tumors).

  提供了对CB2大麻素受体具有特异性的大麻素类似物。这些类似物是1-甲氧基-、1-去氧-11-羟基-和11-羟基-1-甲氧基-Δ8-四氢大麻酚以及1-烷基-3(1-萘酰)吲哚。这些化合物对于治疗疼痛（尤其是由炎症引起的疼痛）和癌症（尤其是胶质瘤）具有用途。
• Amidino derivatives and their use as thrombin inhibitors
  申请人：AstraZeneca AB

  公开号：US06265397B1

  公开（公告）日：2001-07-24

  There is provided compounds of formula I, wherein R1, Rx, Y, Ry, n and B have meanings given in the description which are useful as competitive inhibitors of trypsin-like proteases, such as thrombin, and in particular in the treatment of conditions where inhibition of thrombin is required (e.g. thrombosis) or as anticoagulants.

  提供了符合式I的化合物，其中R1、Rx、Y、Ry、n和B的含义如描述中所述，这些化合物可作为胰蛋白酶样蛋白酶的竞争性抑制剂，例如凝血酶，在需要抑制凝血酶的情况下特别适用（例如血栓形成），或作为抗凝剂。
• New amidino derivatives and their use as thrombin inhibitors
  申请人：AstraZeneca AB

  公开号：US20020022612A1

  公开（公告）日：2002-02-21

  There is provided compounds of formula I, 1 wherein R 1 , R x , Y, R y , n and B have meanings given in the description which are useful as competitive inhibitors of trypsin-like proteases, such as thrombin, and in particular in the treatment of conditions where inhibition of thrombin is required (e.g. thrombosis) or as anticoagulants.

  提供了化合物I,1的公式，其中R1、Rx、Y、Ry、n和B的含义如描述中所给，其可作为竞争性蛋白酶抑制剂，如凝血酶，尤其在需要抑制凝血酶的情况下（例如血栓形成）或作为抗凝剂的治疗中有用。
• The Synthesis of 2- and 6-Substituted Derivatives of 20-Methylcholanthrene¹
  作者：Louis F. Fieser、Victor Desreux

  DOI：10.1021/ja01276a063

  日期：1938.9
• NEW AMIDINO DERIVATIVES AND THEIR USE AS THROMBIN INHIBITORS
  申请人：AstraZeneca AB

  公开号：EP1012140A1

  公开（公告）日：2000-06-28