2,3-dimethoxynaphthalene-1-carboxylic acid | 91903-55-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-dimethoxynaphthalene-1-carboxylic acid
• 英文别名: 2,3-dimethoxy-1-naphthoic acid；2.3-Dimethoxynaphthalin-1-carbonsaeure；2.3-Dimethoxy-1-carboxy-naphthalin；2,3-dimethoxy-1-naphthalenecarboxylic acid
• CAS: 91903-55-8
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: ZRDWGUKPAHRELS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-dimethoxynaphthalene-1-carboxylic acid 在 氯化亚砜 、 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 78.0h， 生成 (-)-(4S)-4-isopropyl-2-(2,3-dimethoxynaphthalene-1-yl)-4,5-dihydroxazole
  参考文献：
  名称：

  Atropisomerism of 2,2'-Binaphthalenes

  摘要：

  合成非对映富集取代的 (4S)-4-异丙基-2-(2,2′-联萘-1-基)-4,5-二氢恶唑 从取代的 2-萘基溴化镁和 (4S)-4-异丙基-2-(2-甲氧基萘-1-基)-4,5-二氢恶唑 (4)和 (4S)-4-异丙基-2-(2,3-二甲氧基萘-1-基)-4,5-二氢恶唑 (5) 进行了描述。产品噁唑啉被转化为多种 衍生物，并测定了其中几种衍生物内旋转的自由能垒。 衍生物的内旋转自由能障。X 射线晶体结构和 结构和 c.d. 光谱。 (S,1S)-N-[2-羟基-1-(异丙基)乙基]-3-甲氧基-1′,N-二甲基-2,2′-联萘-1-甲酰胺 (22) 和 (22) 和 (R,4S)-4-异丙基-3-甲基-2-(1′,2′,4′-三甲基-2,2′-萘-1-基)-4,5-二氢恶唑鎓碘化物 (38) 碘化物 (38) 的绝对构型。 通过比较 2,2′-联萘的 c.d. 光谱和化合物（22）的 c.d. 光谱，可以确定所有合成 2,2′-联萘的绝对构型。 与化合物 (22) 和 (38) 的 c.d 光谱进行比较，从而确定了所有合成 2,2′-萘的绝对构型。

  DOI：

  10.1071/ch00122
• 作为产物：
  描述：

  2,3-二甲氧基-1-萘醛 在 potassium permanganate 、 sodium carbonate 作用下， 以 水 、 丙酮 为溶剂， 以61%的产率得到2,3-dimethoxynaphthalene-1-carboxylic acid
  参考文献：
  名称：

  N-(2-phenyl-4-piperidinybutyl)-5,6,7,8-tetrahydro-1-naphthalenecarboxamides and their use as neurokinin 1 (NK1) and/or neurokinin 2 (NK2) receptor antagonists

  摘要：

  式（I）的化合物，其中R2是一个可以被取代的5,6,7,8-四氢萘基团（在此定义的其余基团），以及含有这些化合物的药物组合物和使用这些化合物治疗NK1和/或NK2受体拮抗有益的方法。

  公开号：

  US06403601B1

文献信息

• COFERONS AND METHODS OF MAKING AND USING THEM
  申请人：Barany Francis

  公开号：US20120295874A1

  公开（公告）日：2012-11-22

  The present invention is directed to a monomer useful in preparing therapeutic compounds. The monomer includes one or more pharmacophores which potentially binds to a target molecule with a dissociation constant of less than 300 μM and a linker element connected to the pharmacophore. The linker element has a molecular weight less than 500 daltons, is connected, directly or indirectly through a connector, to the pharmacophore.

  本发明涉及一种用于制备治疗性化合物的单体。该单体包括一个或多个可与目标分子结合的药效团，其解离常数小于300微摩尔，以及与药效团连接的连接元素。所述连接元素的分子量小于500道尔顿，通过直接连接或通过连接器间接与药效团相连。
• <i>ortho</i>-Lithium/Magnesium Carboxylate-Driven Aromatic Nucleophilic Substitution Reactions on Unprotected Naphthoic Acids
  作者：Regadia Aissaoui、Arnaud Nourry、Ariane Coquel、Thi Thanh Hà Dao、Aicha Derdour、Jean-Jacques Helesbeux、Olivier Duval、Anne-Sophie Castanet、Jacques Mortier

  DOI：10.1021/jo202017z

  日期：2012.1.6

  acids furnishing substituted naphthoic acids occurs in good to excellent yields upon reaction with alkyl/vinyl/aryl organolithium and Grignard reagents, in the absence of a metal catalyst without the need to protect the carboxyl (CO2H) group. This novel nucleophilic aromatic substitution is presumed to proceed via a precoordination of the organometallic with the substrate, followed by an addition/elimination

  在不需要金属催化剂的情况下，与烷基/乙烯基/芳基有机锂和格利雅试剂反应后，提供取代萘酸的1-萘甲酸和2-萘甲酸中的邻氟或甲氧基取代反应的收率非常好。保护羧基（CO 2 H）。据推测，该新的亲核芳族取代是通过有机金属与底物的预配位，然后添加/消除来进行的。
• [EN] NAPHTHALENECARBOXAMIDES AS TACHYKININ RECEPTOR ANTAGONISTS<br/>[FR] NAPHTALENE-CARBOXAMIDES UTILISES EN TANT QU'ANTAGONISTES DES RECEPTEURS DES TACHYKININES
  申请人：ZENECA LTD

  公开号：WO2000020389A1

  公开（公告）日：2000-04-13

  A compound having formula (I) wherein R1 is oxo, -ORa, -OC(=O)Rb; or (A); R2 is H; or R?1 is -ORc and R2 is -ORd; or R1 and R2¿ together form -O(CH¿2?)mO-; and any pharmaceutically-acceptable salt thereof along with their use in treating depression, anxiety, asthma, rheumatoid arthritis, Alzheimer's disease, cancer, schizophrenia, oedema, allergic rhinitis, inflammation, pain, gastrointestinal-hypermotility, anxiety, emesis, Huntington's disease, psychoses including depression, hypertension, migraine, bladder hypermotility, or urticaria, along with methods of making the compounds and pharmaceutical compositions containing the compounds.

  化合物式(I)的化合物，其中R1是氧代、-ORa、-OC（=O）Rb；或（A）；R2是H；或者R1是-ORc且R2是-ORd；或者R1和R2在一起形成-O（CH2）mO-；以及其任何药学上可接受的盐，用于治疗抑郁症、焦虑症、哮喘、类风湿性关节炎、阿尔茨海默病、癌症、精神分裂症、水肿、过敏性鼻炎、炎症、疼痛、胃肠过度运动、焦虑症、呕吐、亨廷顿病、包括抑郁症、高血压、偏头痛、膀胱过度运动或荨麻疹的方法，以及制备这些化合物和含有这些化合物的制药组合物。
• Naphthalenecarboxamides as tachykinin receptor antagonists
  申请人：AstraZeneca AB

  公开号：EP1433783A2

  公开（公告）日：2004-06-30

  A compound having the formula (I) wherein R1 is oxo, -ORa, -OC(=O)Rb; or (A); R2 is H; or R1 is -ORc and R2 is -ORd; or R1 and R2 together form -O(CH2)mO-; R3 is H or alkyl; R4, R5 and R6 are independently selected from hydroxy, cyano, nitro, trifluoromethoxy, trifluoromethyl, alkylsulfonyl, halo, alkoxy, alkyl, cyanoalkyl, alkenyl, alkynyl, carboxy, alkoxy-carbonyl, carbamoyl, alkylcarbamoyl, di-alkylcarbamoyl, alkanoyl, alkanoylamino, aminosulfonyl, and substituted alkyl; or R4 and R5 together form -OCH2O- or -OC(CH3)2O-; R6 may additionally be hydrogen; R7 is substituted phenyl; R8 is selected from hydrogen, hydroxy, alkoxy, alkanoyloxy, alkanoyl, alkoxycarbonyl, alkanoylamino, alkyl, carbamoyl, alkylcarbamoyl, and bis(alkyl)carbamoyl; Ra is hydrogen or alkyl; Rb is alkyl, aryl or arylalkyl; Rc and Rd are independently selected from alkyl; m is 2, 3, or 4; and X1 and X2 are independently H or halogen, wherein at least one of X1 and X2 are halogen; and any pharmaceutically-acceptable salt thereof along with their use in treating depression, anxiety, asthma, rheumatoid arthritis, Alzheimer's disease, cancer, schizophrenia, oedema, allergic rhinitis, inflammation, pain, gastrointestinal-hypermotility, anxiety, emesis, Huntington's disease, psychoses including depression, hypertension, migraine, bladder hypermotility, or urticaria, along with methods of making the compounds and pharmaceutical compositions containing the compounds.

  具有式 (I) 的化合物 其中 R1 是氧代、-ORa、-OC(=O)Rb；或 (A)； R2 是 H；或 R1 是-ORc，R2 是-ORd；或 R1 和 R2 共同形成-O(CH2)mO-； R3 是 H 或烷基；R4、R5 和 R6 独立选自羟基、氰基、硝基、三氟甲氧基、三氟甲基、烷基磺酰基、卤代、烷氧基、烷基、氰基烷基、烯基、炔基、羧基、烷氧基羰基、氨基甲酰基、烷基氨基甲酰基、二烷基氨基甲酰基、烷酰基、烷酰氨基、氨基磺酰基和取代烷基；或 R4 和 R5 共同形成 -O O- 或 -OC(CH3)2O-；R6 还可以是氢；R7 是取代的苯基；R8 选自氢、羟基、烷氧基、烷酰氧基、烷酰基、烷氧羰基、烷酰氨基、烷基、氨基甲酰基、烷基氨基甲酰基和双(烷基)氨基甲酰基；Ra 是氢或烷基；Rb 是烷基、芳基或芳烷基；Rc 和 Rd 独立地选自烷基；m 是 2、3 或 4；以及 X1 和 X2 独立地是 H 或卤素，其中 X1 和 X2 中至少有一个是卤素；及其任何药学上可接受的盐，以及它们在治疗抑郁症、焦虑症、哮喘、类风湿性关节炎、阿尔茨海默病、癌症、精神分裂症、水肿、过敏性鼻炎、炎症、疼痛、胃肠道过度运动、焦虑症、呃逆、亨廷顿氏病、包括抑郁症在内的精神病、高血压、偏头痛、膀胱过度运动或荨麻疹中的用途，以及制造这些化合物和含有这些化合物的药物组合物的方法。
• 6,7-Dimethoxy-2-phenethyl-1,2,3,4-tetrahydroisoquinoline amides and corresponding ester isosteres as multidrug resistance reversers
  作者：Laura Braconi、Gianluca Bartolucci、Marialessandra Contino、Niccolò Chiaramonte、Roberta Giampietro、Dina Manetti、Maria Grazia Perrone、Maria Novella Romanelli、Nicola Antonio Colabufo、Chiara Riganti、Silvia Dei、Elisabetta Teodori

  DOI：10.1080/14756366.2020.1747449

  日期：2020.1.1

  Aiming to deepen the structure-activity relationships of the two P-glycoprotein (P-gp) modulators elacridar and tariquidar, a new series of amide and ester derivatives carrying a 6,7-dimethoxy-2-phenethyl-1,2,3,4-tetrahydroisoquinoline scaffold linked to different methoxy-substituted aryl moieties were synthesised. The obtained compounds were evaluated for their P-gp interaction profile and selectivity towards the two other ABC transporters, multidrug-resistance-associated protein-1 and breast cancer resistance protein, showing to be very active and selective versus P-gp. Two amide derivatives, displaying the best P-gp activity, were tested in co-administration with the antineoplastic drug doxorubicin in different cancer cell lines, showing a significant sensitising activity towards doxorubicin. The investigation on the chemical stability of the derivatives towards spontaneous or enzymatic hydrolysis, showed that amides are stable in both models while some ester compounds were hydrolysed in human plasma. This study allowed us to identify two chemosensitizers that behave as non-transported substrates and are characterised by different selectivity profiles.[GRAPHICS].