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Volumn 2, Issue 12, 2011, Pages 896-900

Discovery of a potent retinoid X receptor antagonist structurally closely related to RXR agonist NEt-3IB

Author keywords

agonists; antagonists; nuclear receptors; retinoids; RXR; Synthetic route

Indexed keywords

3 METHYL 7 (5,6,7,8 TETRAHYDRO 5,5,8,8 TETRAMETHYL 3 PROPOXY 2 NAPHTHYL) 2,4,6 OCTATRIENOIC ACID; 6 [N ETHYL N (3 ISOBUTOXY 4 ISOPROPYLPHENYL)AMINO]NICOTINIC ACID; 6 [N ETHYL N (5 ISOBUTOXY 4 ISOPROPYL 2 STYRYLPHENYL)AMINO]NICOTINIC ACID; AMINE; ANILINE DERIVATIVE; BENZENE DERIVATIVE; ELECTROPHILE; ESTER DERIVATIVE; IODINE; PA 452; PALLADIUM; RECEPTOR BLOCKING AGENT; RETINOID X RECEPTOR AGONIST; RETINOID X RECEPTOR ALPHA; RETINOID X RECEPTOR ANTAGONIST; STYRENE DERIVATIVE; UNCLASSIFIED DRUG; UVI 3002;

EID: 83455258276     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml200197e     Document Type: Article
Times cited : (17)

References (33)
  • 3
    • 34848862778 scopus 로고    scopus 로고
    • Design of selective nuclear receptor modulators: RAR and RXR as a case study
    • DOI 10.1038/nrd2398, PII NRD2398
    • de Lera, A. R.; Bourguet, W.; Altucci, L.; Gronemeyer, H. Design of selective nuclear receptor modulators: RAR and RXR as a case study Nat. Rev. Drug Discovery 2007, 6, 811-820 (Pubitemid 47504872)
    • (2007) Nature Reviews Drug Discovery , vol.6 , Issue.10 , pp. 811-820
    • De Lera, A.R.1    Bourguet, W.2    Altucci, L.3    Gronemeyer, H.4
  • 6
    • 1642304065 scopus 로고    scopus 로고
    • Structural determinants of allosteric ligand activation in RXR heterodimers
    • DOI 10.1016/S0092-8674(04)00119-9, PII S0092867404001199
    • Shulman, A. I.; Larson, C.; Mangelsdorf, D. J.; Ranganathan, R. Structural determinants of allosteric ligand activation in RXR heterodimers Cell 2004, 116, 417-429 (Pubitemid 38366318)
    • (2004) Cell , vol.116 , Issue.3 , pp. 417-429
    • Shulman, A.I.1    Larson, C.2    Mangelsdorf, D.J.3    Ranganathan, R.4
  • 7
    • 23444431623 scopus 로고    scopus 로고
    • Retinoid X receptor heterodimers in the metabolic syndrome
    • DOI 10.1056/NEJMra043590
    • Shulman, A. I.; Mangelsdorf, D. J. Retinoid X receptor heterodimers in the metabolic syndrome N. Engl. J. Med. 2005, 353, 604-615 (Pubitemid 41138942)
    • (2005) New England Journal of Medicine , vol.353 , Issue.6 , pp. 604-615
    • Shulman, A.I.1    Mangelsdorf, D.J.2
  • 8
    • 37649030471 scopus 로고    scopus 로고
    • Therapeutic potential of retinoid X receptor modulators for the treatment of the metabolic syndrome
    • Pinaire, J. A.; Reifel-Miller, A. Therapeutic potential of retinoid X receptor modulators for the treatment of the metabolic syndrome PPAR Res. 2007, 2007, 94156
    • (2007) PPAR Res. , vol.2007 , pp. 94156
    • Pinaire, J.A.1    Reifel-Miller, A.2
  • 9
    • 0032966295 scopus 로고    scopus 로고
    • The RXR agonist LG100268 causes hepatomegaly, improves glycaemic control and decreases cardiovascular risk and cachexia in diabetic mice suffering from pancreatic beta-cell dysfunction
    • DOI 10.1007/s001250051193
    • Lenhard, J. M.; Lancaster, M. E.; Paulik, M. A.; Weiel, J. E.; Binz, J. G.; Sundseth, S. S.; Gaskill, B. A.; Lightfoot, R. M.; Brown, H. R. The RXR agonist LG100268 causes hepatomegaly, improves glycaemic control and decreases cardiovascular risk and cachexia in diabetic mice suffering from pancreatic beta-cell dysfunction Diabetologia 1999, 42, 545-554 (Pubitemid 29196004)
    • (1999) Diabetologia , vol.42 , Issue.5 , pp. 545-554
    • Lenhard, J.M.1    Lancaster, M.E.2    Paulik, M.A.3    Weiel, J.E.4    Binz, J.G.5    Sundseth, S.S.6    Gaskill, B.A.7    Lightfoot, R.M.8    Brown, H.R.9
  • 10
    • 0035581103 scopus 로고    scopus 로고
    • Retinoid X receptor agonist elevation of serum triglycerides in rats by potentiation of retinoic acid receptor agonist induction or by action as single agents
    • DOI 10.1016/S0006-2952(01)00803-6, PII S0006295201008036
    • Standeven, A. M.; Thacher, S. M.; Yuan, Y. D.; Escobar, M.; Vuligonda, V.; Beard, R. L.; Chandraratna, R. A. Retinoid X receptor agonist elevation of serum triglycerides in rats by potentiation of retinoic acid receptor agonist induction or by action as single agents Biochem. Pharmacol. 2001, 62, 1501-1509 (Pubitemid 33145293)
    • (2001) Biochemical Pharmacology , vol.62 , Issue.11 , pp. 1501-1509
    • Standeven, A.M.1    Thacher, S.M.2    Yuan, Y.-D.3    Escobar, M.4    Vuligonda, V.5    Beard, R.L.6    Chandraratna, R.A.S.7
  • 12
    • 83255192155 scopus 로고    scopus 로고
    • Modulation of RXR function through ligand design
    • DOI: 10.1016/j.bbalip.2011.04.003. Published Online: April 16, 2011
    • Pérez, E.; Bourguet, W.; Gronemeyer, H.; de Lera, A. R. Modulation of RXR function through ligand design. Biochim. Biophys. Acta, DOI: 10.1016/j.bbalip.2011.04.003. Published Online: April 16, 2011.
    • Biochim. Biophys. Acta
    • Pérez, E.1    Bourguet, W.2    Gronemeyer, H.3    De Lera, A.R.4
  • 14
    • 33645971026 scopus 로고    scopus 로고
    • Cutting Edge: Inhibition of the retinoid X receptor (RXR) blocks T helper 2 differentiation and prevents allergic lung inflammation
    • Grenningloh, R.; Gho, A.; di Lucia, P.; Klaus, M.; Bollag, W.; Ho, I. C.; Sinigaglia, F.; Panina-Bordignon, P. Cutting Edge: Inhibition of the retinoid X receptor (RXR) blocks T helper 2 differentiation and prevents allergic lung inflammation J. Immunol. 2006, 176, 5161-5166
    • (2006) J. Immunol. , vol.176 , pp. 5161-5166
    • Grenningloh, R.1    Gho, A.2    Di Lucia, P.3    Klaus, M.4    Bollag, W.5    Ho, I.C.6    Sinigaglia, F.7    Panina-Bordignon, P.8
  • 17
    • 47649097615 scopus 로고    scopus 로고
    • The first potent subtype-selective retinoid X receptor (RXR) agonist possessing a 3-isopropoxy-4-isopropylphenylamino moiety, NEt-3IP (RXR/β-dual agonist)
    • Takamatsu, K.; Takano, A.; Yakushiji, N.; Morohashi, K.; Morishita, K.; Matsuura, N.; Makishima, M.; Tai, A.; Sasaki, K.; Kakuta, H. The first potent subtype-selective retinoid X receptor (RXR) agonist possessing a 3-isopropoxy-4-isopropylphenylamino moiety, NEt-3IP (RXR/β-dual agonist) ChemMedChem 2008, 3, 780-787
    • (2008) ChemMedChem , vol.3 , pp. 780-787
    • Takamatsu, K.1    Takano, A.2    Yakushiji, N.3    Morohashi, K.4    Morishita, K.5    Matsuura, N.6    Makishima, M.7    Tai, A.8    Sasaki, K.9    Kakuta, H.10
  • 19
    • 0033783346 scopus 로고    scopus 로고
    • Retinoidal pyrimidinecarboxylic acids. Unexpected diaza-substituent effects in retinobenzoic acids
    • Ohta, K.; Kawachi, E.; Inoue, N.; Fukasawa, H.; Hashimoto, Y.; Itai, A.; Kagechika, H. Retinoidal pyrimidinecarboxylic acids. Unexpected diaza-substituent effects in retinobenzoic acids Chem. Pharm. Bull. 2000, 48, 1504-1513
    • (2000) Chem. Pharm. Bull. , vol.48 , pp. 1504-1513
    • Ohta, K.1    Kawachi, E.2    Inoue, N.3    Fukasawa, H.4    Hashimoto, Y.5    Itai, A.6    Kagechika, H.7
  • 22
    • 0036682057 scopus 로고    scopus 로고
    • Novel retinoid X receptor antagonists: Specific inhibition of retinoid synergism in RXR-RAR heterodimer actions
    • DOI 10.1021/jm0255320
    • Takahashi, B.; Ohta, K.; Kawachi, E.; Fukasawa, H.; Hashimoto, Y.; Kagechika, H. Novel retinoid X receptor antagonists: Specific inhibition of retinoid synergism in RXR-RAR heterodimer actions J. Med. Chem. 2002, 45, 3327-3330 (Pubitemid 34824021)
    • (2002) Journal of Medicinal Chemistry , vol.45 , Issue.16 , pp. 3327-3330
    • Takahashi, B.1    Ohta, K.2    Kawachi, E.3    Fukasawa, H.4    Hashimoto, Y.5    Kagechika, H.6
  • 23
    • 19944430311 scopus 로고    scopus 로고
    • Characterization of the interaction between retinoic acid receptor/retinoid X receptor (RAR/RXR) heterodimers and transcriptional coactivators through structural and fluorescence anisotropy studies
    • Pogenberg, V.; Guichou, J. F.; Vivat-Hannah, V.; Kammerer, S.; Pérez, E.; Germain, P.; de Lera, A. R.; Gronemeyer, H.; Royer, C. A.; Bourguet, W. Characterization of the interaction between retinoic acid receptor/retinoid X receptor (RAR/RXR) heterodimers and transcriptional coactivators through structural and fluorescence anisotropy studies J. Biol. Chem. 2005, 280, 1625-1633
    • (2005) J. Biol. Chem. , vol.280 , pp. 1625-1633
    • Pogenberg, V.1    Guichou, J.F.2    Vivat-Hannah, V.3    Kammerer, S.4    Pérez, E.5    Germain, P.6    De Lera, A.R.7    Gronemeyer, H.8    Royer, C.A.9    Bourguet, W.10
  • 25
    • 43949125180 scopus 로고    scopus 로고
    • Sequence of intramolecular carbonylation and asymmetric hydrogenation reactions: Highly regio- and enantioselective synthesis of medium ring tricyclic lactams
    • DOI 10.1021/ja7111417
    • Lu, S. M.; Alper, H. Sequence of intramolecular carbonylation and asymmetric hydrogenation reactions: Highly regio- and enantioselective synthesis of medium ring tricyclic lactams J. Am. Chem. Soc. 2008, 130, 6451-6455 (Pubitemid 351706107)
    • (2008) Journal of the American Chemical Society , vol.130 , Issue.20 , pp. 6451-6455
    • Lu, S.-M.1    Alper, H.2
  • 26
    • 0028337412 scopus 로고
    • Aryl couplings with heterogeneous palladium catalysts
    • DOI 10.1016/S0040-4039(00)76884-5
    • Marck, G.; Villiger, A.; Buchecker, R. Aryl couplings with heterogeneous palladium catalysts Tetrahedron Lett. 1994, 35, 3277-3280 (Pubitemid 24163976)
    • (1994) Tetrahedron Letters , vol.35 , Issue.20 , pp. 3277-3280
    • Marck, G.1    Villiger, A.2    Buchecker, R.3
  • 27
    • 0001546929 scopus 로고
    • Synthesis of 7-substituted indolactam-V: An introduction of hydrophobic moieties on the indole ring
    • Y. Endo, R.; Sato, Y.; Shudo, K. Synthesis of 7-substituted indolactam-V: An introduction of hydrophobic moieties on the indole ring Tetrahedron 1987, 43, 2241-2247
    • (1987) Tetrahedron , vol.43 , pp. 2241-2247
    • Endo R, Y.1    Sato, Y.2    Shudo, K.3
  • 28
    • 0030873988 scopus 로고    scopus 로고
    • An ammonia equivalent for the palladium-catalyzed amination of aryl halides and triflates
    • DOI 10.1016/S0040-4039(97)01465-2, PII S0040403997014652
    • Wolfe, J. P.; Ahman, J.; Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. An ammonia equivalent for the palladium-catalyzed amination of aryl halides and triflates Tetrahedron Lett. 1997, 38, 6367-6370 (Pubitemid 27368167)
    • (1997) Tetrahedron Letters , vol.38 , Issue.36 , pp. 6367-6370
    • Wolfe, J.P.1    Ahman, J.2    Sadighi, J.P.3    Singer, R.A.4    Buchwald, S.L.5
  • 30
    • 0009644628 scopus 로고
    • Some quantitative uses of drug antagonists
    • Arunlakshana, O.; Schild, H. O. Some quantitative uses of drug antagonists Br. J. Pharmacol. 1959, 14, 48-58
    • (1959) Br. J. Pharmacol. , vol.14 , pp. 48-58
    • Arunlakshana, O.1    Schild, H.O.2


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