7,8-Dihydronaphthalene-2-carboxylic acid | 151623-57-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7,8-Dihydronaphthalene-2-carboxylic acid
• CAS: 151623-57-3
• 化学式: C₁₁H₁₀O₂
• mdl: MFCD20655158
• 分子量: 174.199
• InChiKey: PPNYJZJSGMBUPH-UHFFFAOYSA-N

物化性质

• 沸点：
  329.7±31.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7,8-Dihydronaphthalene-2-carboxylic acid 在 N-溴代丁二酰亚胺(NBS) 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 N-溴代乙酰胺 作用下， 以 四氯化碳 、 溶剂黄146 为溶剂， 反应 5.0h， 生成 5-Acetyl-6,8-dibromo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid
  参考文献：
  名称：

  Hapten design and development of an ELISA (enzyme-linked immunosorbent assay) for the detection of the mercapturic acid conjugates of naphthalene

  摘要：

  Measurement of urinary metabolites constitutes a noninvasive method to assess toxic exposure. Naphthalene is a common environmental contaminant showing selective pulmonary toxicity in mice and presumably is involved in development of lung disease in man (Buckpitt, A.R.; Franklin, R.B. Pharmacol. Ther. 1989, 41, 339). A glutathione-based detoxification pathway leads to the formation of the mercapturic acid conjugates [NaphMA 1, (R)-N-acetyl-S-[(1R*,2R*)-1,2-dihydro-1-hydroxy-2-naphthyl]cysteine] and (R)-N-acetyl-S-[(1R*,2R*)-1,2-dihydro-2-hydroxy-1-naphthyl]cysteine] which are excreted in urine. Herein we report the development of an immunoassay for the specific detection of these urinary metabolites. This study confirms the importance of appropriate hapten design and synthesis in controlling the specificity and sensitivity of the immunoassay. Our strategy was to prepare haptens that allow covalent attachment to a carrier protein at a site opposite to the N-acetylcysteine moiety. The antibodies obtained by immunizing six rabbits with these NaphMA derivatives (haptens 13 and 14) have been used for the development of an ELISA (enzyme-linked immunosorbent assay) which detects NaphMA 1 in the range between 100 and 6 pg/mL with an I50 of 29 pg/mL. Its ability to detect these important naphthalene metabolites in human urine is demonstrated.

  DOI：

  10.1021/jo00078a039
• 作为产物：
  描述：

  6-羟基-1-四氢萘酮 在 甲醇 、 sodium tetrahydroborate 、 1,3-双(二苯基膦)丙烷 、 水 、 palladium diacetate 、 对甲苯磺酸 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 29.0h， 生成 7,8-Dihydronaphthalene-2-carboxylic acid
  参考文献：
  名称：

  FXR受体激动剂

  摘要：

  本发明属于医药技术领域，具体涉及式(I)所示的化合物、其药学上可接受的盐、酯或其立体异构体，R1、R2、R3、M1、M2、m、n、Q、L、环A、环B、环C如说明书中所定义；本发明还涉及这些化合物的制备方法及在用于制备治疗和/或预防由FXR受体介导的非酒精性脂肪肝、原发性胆汁性肝硬化、脂质代谢紊乱、糖尿病并发症及恶性肿瘤等相关疾病的药物中的应用。

  公开号：

  CN109320517B

文献信息

• [EN] GEMINAL SUBSTITUTED QUINUCLIDINE AMIDE COMPOUNDS AS AGONISTS OF ALPHA-7 NICOTINIC ACETYLCHOLINE RECEPTORS<br/>[FR] COMPOSÉS AMIDE DE QUINUCLIDINE À SUBSTITUANTS GÉMINAL, EN TANT QU'AGONISTES DES RÉCEPTEURS NICOTINIQUES DE L'ACÉTYLCHOLINE Α7
  申请人：FORUM PHARMACEUTICALS INC

  公开号：WO2016100184A1

  公开（公告）日：2016-06-23

  The present invention relates to novel geminal substituted quinuclidine amide compounds, and pharmaceutical compositions of the same, that are suitable as agonists or partial agonists of α7- nAChR, and methods of preparing these compounds and compositions, and the use of these compounds and compositions in methods of maintaining, treating and/or improving cognitive function. In particular, methods of administering the compound or composition to a patient in need thereof, for example a patient with a cognitive deficiency and/or a desire to enhance cognitive function, that may derive a benefit therefrom.

  本发明涉及新型的伏立康定酰胺化合物，以及相应的药物组合物，其适用于作为α7-nAChR的激动剂或部分激动剂，并且涉及制备这些化合物和组合物的方法，以及在维持、治疗和/或改善认知功能的方法中使用这些化合物和组合物，特别是将该化合物或组合物用于需要的患者的给药方法，例如患有认知缺陷和/或希望增强认知功能的患者，这些患者可能从中获益。
• Enantioselective Enzymatic Naphthoyl Ring Reduction
  作者：Max Willistein、Julian Haas、Jonathan Fuchs、Sebastian Estelmann、Sascha Ferlaino、Michael Müller、Steffen Lüdeke、Matthias Boll

  DOI：10.1002/chem.201802683

  日期：2018.8.27

  intermediate during 2‐NCoA reduction, whereas the subsequent reduction of 5,6‐dihydro‐2‐NCoA is suggested to proceed via an unprecedented cationic transition state. Using vibrational circular dichroism (VCD) spectroscopy, we demonstrate that both enzymatic reductions are highly stereoselective in D2O, providing an enantioselective pathway to products inaccessible by Birch reduction. Moreover, we demonstrate

  通过单电子转移步骤进行的芳香烃的桦木还原取决于碱金属，氨和低温反应条件。相反，2-萘甲酰基辅酶A（2-NCoA）和5,6-二氢-2-NCoA（5,6-DHNCoA）还原酶在环境温度下催化萘甲环体系的两个两电子还原为四氢萘甲酰辅酶A。温度。使用多种底物类似物，我们为2-NCoA还原过程中的Meisenheimer复杂类似中间体提供了证据，而随后5,6-二氢-2-NCoA的还原则建议通过前所未有的阳离子过渡态进行。使用振动圆二色性（VCD）光谱，我们证明了两种酶还原在D 2中都具有高度立体选择性O，为桦木还原无法获得的产品提供对映选择性途径。此外，我们证明了VCD光谱法能够确定同位素引起的脂环式立体中心的绝对构型。
• Hapten design and development of an ELISA (enzyme-linked immunosorbent assay) for the detection of the mercapturic acid conjugates of naphthalene
  作者：Maria Pilar Marco、Bruce D. Hammock、Mark J. Kurth

  DOI：10.1021/jo00078a039

  日期：1993.12

  Measurement of urinary metabolites constitutes a noninvasive method to assess toxic exposure. Naphthalene is a common environmental contaminant showing selective pulmonary toxicity in mice and presumably is involved in development of lung disease in man (Buckpitt, A.R.; Franklin, R.B. Pharmacol. Ther. 1989, 41, 339). A glutathione-based detoxification pathway leads to the formation of the mercapturic acid conjugates [NaphMA 1, (R)-N-acetyl-S-[(1R*,2R*)-1,2-dihydro-1-hydroxy-2-naphthyl]cysteine] and (R)-N-acetyl-S-[(1R*,2R*)-1,2-dihydro-2-hydroxy-1-naphthyl]cysteine] which are excreted in urine. Herein we report the development of an immunoassay for the specific detection of these urinary metabolites. This study confirms the importance of appropriate hapten design and synthesis in controlling the specificity and sensitivity of the immunoassay. Our strategy was to prepare haptens that allow covalent attachment to a carrier protein at a site opposite to the N-acetylcysteine moiety. The antibodies obtained by immunizing six rabbits with these NaphMA derivatives (haptens 13 and 14) have been used for the development of an ELISA (enzyme-linked immunosorbent assay) which detects NaphMA 1 in the range between 100 and 6 pg/mL with an I50 of 29 pg/mL. Its ability to detect these important naphthalene metabolites in human urine is demonstrated.
• FXR受体激动剂
  申请人：轩竹生物科技有限公司

  公开号：CN109320517B

  公开（公告）日：2021-08-17

  本发明属于医药技术领域，具体涉及式(I)所示的化合物、其药学上可接受的盐、酯或其立体异构体，R1、R2、R3、M1、M2、m、n、Q、L、环A、环B、环C如说明书中所定义；本发明还涉及这些化合物的制备方法及在用于制备治疗和/或预防由FXR受体介导的非酒精性脂肪肝、原发性胆汁性肝硬化、脂质代谢紊乱、糖尿病并发症及恶性肿瘤等相关疾病的药物中的应用。