Synthesis of the trifluoromethylated retinoial aromatic amide - 4-[1-(5,6,7,8-tetrahydro-3-trifluoromethyl-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl]benzoic acid

被引：8
|
作者：
Qing, FL [1 ]
Fan, JF [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Lab Organofluorine Chem, Shanghai 200032, Peoples R China
来源：
JOURNAL OF FLUORINE CHEMISTRY | 1999年 / 96卷 / 02期
基金：
中国国家自然科学基金;
关键词：
retinoids; trifluoromethylation;
D O I：
10.1016/S0022-1139(99)00070-6
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A new methodology was developed for the preparation of an o-trifluoromethylated arylamine. The condensation of 2-amino-3-trifluoromethyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene and terephthalic acid monomethyl ester chloride gave the trifluoromethylated retinoial aromatic amide. The key step in the synthesis is the introduction of the aryl trifluoromethyl group. (C) 1999 Elsevier Science S.A. All rights reserved.
引用
收藏
页码：159 / 161
页数：3
相关论文
共 50 条
  • [21] Studies on the metabolism and disposition of the new retinoid 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)carbamoyl]benzoic acid - 1st communication: Absorption, distribution, metabolism and excretion after topical application and subcutaneous administration in rats
    Mizojiri, KJ
    Okabe, H
    Sugeno, K
    Esumi, Y
    Takaichi, M
    Miyake, T
    Seki, H
    Inaba, A
    ARZNEIMITTEL-FORSCHUNG/DRUG RESEARCH, 1997, 47 (01): : 59 - 69
  • [22] METHYL 6-[(4-BROMOBENZOYLOXY)(5,5,8,8-TETRAMETHYL-5,6,7,8-TETRAHYDRO-2-NAPHTHYL)-METHYL]-2-NAPHTHALENECARBOXYLATE
    GAO, Q
    YU, KL
    MANSURI, MM
    KERNS, EH
    STARRETT, JE
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1995, 51 : 1672 - 1675
  • [23] 4-Hydroxybenzyl Modification of the Highly Teratogenic Retinoid, 4-[(1E)-2-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-1-propen-1-yl]benzoic Acid (TTNPB), Yields a Compound That Induces Apoptosis in Breast Cancer Cells and Shows Reduced Teratogenicity
    Anding, Allyson L.
    Nieves, Nirca J.
    Abzianidze, Victoria V.
    Collins, Michael D.
    Curley, Robert W., Jr.
    Clagett-Dame, Margaret
    CHEMICAL RESEARCH IN TOXICOLOGY, 2011, 24 (11) : 1853 - 1861
  • [24] SYNTHESES AND BIOLOGICAL UTILITY OF ISOTOPICALLY LABELED 4-[1-(3,5,5,8,8-PENTAMETHYL-5,6,7,8-TETRAHYDRO-2-NAPHTHYL)ETHENYL)BENZOIC ACID (LGD1069)
    ZHANG, L
    BADEA, BA
    ENYEART, D
    BERGER, EM
    MAIS, DE
    BOEHM, MF
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 : 51 - MEDI
  • [25] SYNTHESES AND BIOLOGICAL UTILITY OF ISOTOPICALLY LABELED 4-[1-(3,5,5,8,8-PENTAMETHYL-5,6,7,8-TETRAHYDRO-2-NAPHTHYL)ETHENYL]BENZOIC ACID (LGD1069)
    ZHANG, L
    BADEA, BA
    ENYEART, D
    BERGER, EM
    MAIS, DE
    BOEHM, MF
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 : 21 - MEDI
  • [26] Liarozole markedly increases all trans-retinoic acid toxicity in mouse limb bud cell cultures:: A model to explain the potency of the aromatic retinoid (E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylenyl)-1-propenyl] benzoic acid
    Pignatello, MA
    Kauffman, FC
    Levin, AA
    TOXICOLOGY AND APPLIED PHARMACOLOGY, 2002, 178 (03) : 186 - 194
  • [27] Syntheses and structure-activity relationships of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-quinoxaline derivatives with retinoic acid receptor α agonistic activity
    Kikuchi, K
    Hibi, S
    Yoshimura, H
    Tokuhara, N
    Tai, K
    Hida, T
    Yamauchi, T
    Nagai, M
    JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (03) : 409 - 419
  • [28] Modeling, Synthesis, and Biological Evaluation of Potential Retinoid X Receptor (RXR)-Selective Agonists: Analogues of 4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic Acid (Bexarotene) and 6-(Ethyl(5,5,8,8-tetrahydronaphthalen-2-yl)amino)nicotinic Acid (NEt-TMN)
    Heck, Michael C.
    Wagner, Carl E.
    Shahani, Pritika H.
    MacNeill, Maid
    Grozic, Aleksandra
    Darwaiz, Tamana
    Shimabuku, Micah
    Deans, David G.
    Robinson, Nathan M.
    Salama, Samer H.
    Ziller, Joseph W.
    Ma, Ning
    van der Vaart, Arjan
    Marshall, Pamela A.
    Jurutka, Peter W.
    JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (19) : 8924 - 8940
  • [29] AROMATIC RETINOIDS .2. A SHORT AND CONVENIENT ROUTE TO 5-(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-ANTHRACENYL)-2-FURAN AND 2-THIOPHENE CARBOXYLIC-ACIDS
    EUSTACHE, J
    BERNARDON, JM
    SHROOT, B
    TETRAHEDRON LETTERS, 1988, 29 (35) : 4409 - 4410
  • [30] BICYCLIC ALPHA-AMINO-ACIDS, .4. SYNTHESIS OF 3-(1,2,3,4-TETRAHYDRO-1-NAPHTHALENYL)-AND 3-(5,6,7,8-TETRAHYDRO-5-QUINOLINYL)-ALANINE
    REIMANN, E
    DAMMERTZ, W
    ARCHIV DER PHARMAZIE, 1983, 316 (04) : 297 - 302
12345