Discovery, synthetic methodology, and biological evaluation for antiphotoaging activity of bicyclic[1,2,3]triazoles: In vitro and in vivo studies

Journal of Medicinal Chemistry

Volumn 56, Issue 13, 2013, Pages 5422-5435

  Hsieh, Hsin Yu ^b   Lee, Wen Chun ^a   Senadi, Gopal Chandru ^a   Hu, Wan Ping ^b   Liang, Jium Jia ^a   Tsai, Tong Rong ^b   Chou, Yu Wei ^b   Kuo, Kung Kai ^b   Chen, Chung Yu ^b   Wang, Jeh Jeng ^a  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^b KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; 2 (5,6 DIHYDRO 4H PYRROLO[1,2 E][1,2,3]TRIAZOL 3 YL)BENZENAMINE; 2 [4,5,6,7 TETRAHYDRO[1,2,3]TRIAZOLO[1,5 A]PYRIDIN 3 YL]PHENYLAMINE; 3 (2 TRIFLUOROPHENYL) 4,5,6,7 TETRAHYDRO[1,2,3]TRIAZOLO[1,5A]PYRIDINE; 3 (2 TRIFLUOROPHENYL) 5,6 DIHYDRO 4H PYRROLO[1,2 C ][1,2,3]TRIAZOLE; 3 (3 METHOXYPHENYL) 4,5,6,7 TETRAHYDRO[1,2,3]TRIAZOLO[1,5A]PYRIDINE; 3 (3 METHOXYPHENYL) 5,6 DIHYDRO 4H PYRROLO[1,2 C ][1,2,3]TRIAZOLE; 3 (3 NITROPHENYL) 4,5,6,7 TETRAHYDRO[1,2,3]TRIAZOLO[1,5A]PYRIDINE; 3 (3 NITROPHENYL) 5,6 DIHYDRO 4H PYRROLO[1,2 C ][1,2,3]TRIAZOLE; 3 (4 METHOXYPHENYL) 4,5,6,7 TETRAHYDRO[1,2,3]TRIAZOLO[1,5A]PYRIDINE; 3 (4 METHOXYPHENYL) 5,6 DIHYDRO 4H PYRROLO[1,2 C ][1,2,3]TRIAZOLE; 3 (4 NITROPHENYL) 4,5,6,7 TETRAHYDRO[1,2,3]TRIAZOLO[1,5A]PYRIDINE; 3 (4 NITROPHENYL) 5,6 DIHYDRO 4H PYRROLO[1,2 C ][1,2,3]TRIAZOLE; 3 ALLYL 4,5,6,7 TETRAHYDRO[1,2,3]TRIAZOLO[1,5A]PYRIDINE; 3 ALLYL 5,6 DIHYDRO 4H PYRROLO[1,2 E ][1,2,3]TRIAZOLE; 3 PHENYL 4,5,6,7 TETRAHYDRO[1,2,3]TRIAZOLO[1,5 A]PYRIDINE; 3 PHENYL 5,6 DIHYDRO 4H PYRROLO[1,2 C ][1,2,3]TRIAZOLE; 3 PHENYLETHYNYL 5,6 DIHYDRO 4H PYRROLO[1,2 C ][1,2,3]TRIAZOLE; BETA GALACTOSIDASE; ELASTIN; FIBRONECTIN; INTERSTITIAL COLLAGENASE; MESSENGER RNA; PROCOLLAGEN; TISSUE INHIBITOR OF METALLOPROTEINASE 1; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIPHOTOAGING ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MITOCHONDRIAL MEMBRANE POTENTIAL; MOUSE; NONHUMAN; PHOTOAGING; SENESCENCE; SKIN FIBROBLAST; ULTRAVIOLET A RADIATION;

ANIMALS; CELLS, CULTURED; COLLAGEN TYPE I; DRUG DESIGN; ELASTIN; FEMALE; FIBROBLASTS; FIBRONECTINS; GENE EXPRESSION; HUMANS; IMMUNOBLOTTING; MATRIX METALLOPROTEINASE 1; MEMBRANE POTENTIAL, MITOCHONDRIAL; MICE; MICE, INBRED ICR; MODELS, CHEMICAL; MOLECULAR STRUCTURE; REACTIVE OXYGEN SPECIES; REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION; SKIN; SKIN AGING; TISSUE INHIBITOR OF METALLOPROTEINASE-1; TRIAZOLES; ULTRAVIOLET RAYS;

EID: 84880171938     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm400394s     Document Type: Article

References (71)

1. Pallela, R.; Young, Y. N.; Kim, S. K. Anti-photoaging and photoprotective compounds derived from marine organisms Mar. Drugs 2010, 8, 1189-1202
2. Agar, N. S.; Halliday, G. M.; Barnetson, R.; Ananthaswamy, H. N.; Wheeler, M.; Jones, A. M. The basal layer in human squamous tumors harbors more UVA than UVB fingerprint mutations: a role for UVA in human skin carcinogenesis Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 4954-4959
3. Ryu, B.; Qian, Z. J.; Kim, M. M.; Nam, K. W.; Kim, S. K. Anti-photoaging activity and inhibition of matrix metalloproteinase (MMP) by marine red alga, Corallina pilulifera methanol extract Radiat. Phys. Chem. 2009, 78, 98-105
4. For review see: Rittie, L.; Fisher, G. J. UV-light-induced signal cascades and skin aging Ageing Res Rev. 2002, 1, 705-720
5. Kehrer, J. P. Free radicals as mediators of tissue injury and disease Crit. Rev. Toxicol. 1993, 23, 21-48
6. Aruoma, O. I. Nutrition and health aspects of free radicals and antioxidants Food Chem. Toxicol. 1994, 62, 671-683
7. Fiers, W.; Beyaert, R.; Declercq, W.; Vandenabeele, P. More than one way to die: apoptosis, necrosis and reactive oxygen damage Oncogene. 1999, 18, 7719-7730
8. Record, I. R.; Dreosti, I. E.; Konstantinopoulos, M.; Buckley, R. A. The influence of topical and systemic vitamin E on ultraviolet light-induced skin damage in hairless mice Nutr. Cancer. 1991, 16, 219-226
9. Kawaguchi, Y.; Tanaka, H.; Okada, T.; Konishi, H.; Takahashi, M.; Ito, M.; Asai, J. The effects of ultraviolet A and reactive oxygen species on the mRNA expression of 72-kDa type IV collagenase and its tissue inhibitor in cultured human dermal fibroblasts Arch. Dermatol. Res. 1996, 288, 39-44
10. For review see: Krutmann, J.; Schroeder, P. Role of mitochondria in photoaging of human skin: the defective powerhouse model J. Invest. Dermatol. Symp. Proc. 2009, 14, 44-49
11. Gogvadze; Zhivotovsky, B. Alteration of mitochondrial function and cell sensitization to death J. Bioenerg. Biomembr. 2007, 39, 23-30
12. Lee, P. L.; Weelden, H. V.; Bruijnzeel, P. L. B. Neutrophil infiltration in normal human skin after exposure to different ultraviolet radiation sources Photochem. Photobiol. 2008, 84, 1528-1534
13. Bode, W.; Fernandez-Catalan, C.; Tschesche, H.; Grams, F.; Nagase, H.; Maskos, K. Structural properties of matrix metalloproteinases Cell. Mol. Life Sci. 1999, 55, 639-652
14. Kang, S.; Chung, J. H.; Lee, J. H.; Fisher, G. J.; Wan, Y. S.; Duell, E. A.; Voorhees, J. J. Topical N -acetyl cysteine and genistein prevent ultraviolet-light-induced signaling that leads to photoaging in human skin in vivo J. Invest. Dermatol. 2003, 120, 835-841
15. Sinha, R. P.; Klisch, M.; Gröniger, A.; Häder, D. P. Ultraviolet-absorbing/screening substances in cyanobacteria, phytoplankton and macroalgae J. Photochem. Photobiol., B 1998, 47, 83-94
16. Sinha, R. P.; Singh, S. P.; Häder, D. P. Database on mycosporines and mycosporine-like amino acids (MAAs) in fungi, cyanobacteria, macroalgae, phytoplankton and animals J. Photochem. Photobiol., B 2007, 89, 29-35
17. For a recent review see the following: Tron, G. C.; Pirali, T.; Billington, R. A.; Canonico, P. L.; Sorba, G.; Genazzani, A. A. Click chemistry reactions in medicinal chemistry: applications of the 1,3-dipolar cycloaddition between azides and alkynes Med. Res. Rev. 2008, 28, 278-308
18. Lee, T.; Cho, M.; Ko, S.-Y.; Youn, H. J.; Back, D. J.; Cho, W.-J.; Kang, C.-Y.; Kim, S. Synthesis and evaluation of 1,2,3-triazole containing analogues of the immunostimulant α-GalCer J. Med. Chem. 2007, 50, 585-589
19. Pfaller, M. A.; Messer, S.; Jones, R. N. Activity of a new triazole, Sch 56592, compared with those of four other antifungal agents tested against clinical isolates of Candida spp. and Saccharomyces cerevisiae Antimicrob. Agents Chemother. 1997, 41, 233-235
20. Van Steenis, D. J. V. C.; David, O. R. P.; Van Strijdonck, G. P. F.; Van Maarseveen, J. H.; Reek, J. N. H. Click-chemistry as an efficient synthetic tool for the preparation of novel conjugated polymers Chem. Commun. 2005, 4333-4335
21. Laurent, B. A.; Grayson, S. M. An efficient route to well-defined macrocyclic polymers via "click" cyclization J. Am. Chem. Soc. 2006, 128, 4238-4239
22. Angell, Y. L.; Burgess, K. Peptidomimetics via copper-catalyzed azide-alkyne cycloadditions Chem. Soc. Rev. 2007, 36, 1674-1689 and references therein
23. Arroyave, F. A.; Richard, C. A.; Reynolds, J. R. Efficient synthesis of benzo[1,2- b:6,5- b ′]dithiophene-4,5-dione (BDTD) and its chemical transformations into precursors for π-conjugated materials Org. Lett. 2012, 14, 6138-6141
24. Cheng, H.; Wan, J.; Lin, M. I.; Liu, Y.; Lu, X.; Liu, J.; Xu, Y.; Chen, J.; Tu, Z.; Cheng, Y. S. E.; Ding, K. Design, synthesis, and in vitro biological evaluation of 1 H -1,2,3-triazole-4-carboxamide derivatives as new anti-influenza A agents targeting virus nucleoprotein J. Med. Chem. 2012, 55, 2144-2153
25. Brik, A.; Alexandratos, J.; Lin, Y.-C.; Elder, J. H.; Olson, A. J.; Wlodawer, A.; Goodsell, D. S.; Wong, C.-H. 1,2,3-Triazole as a peptide surrogate in the rapid synthesis of HIV-1 protease inhibitors ChemBioChem 2005, 6, 1167-1169
26. Aufort, M.; Herscovici, J.; Bouhours, P.; Moreau, N.; Girard, C. Synthesis and antibiotic activity of a small molecules library of 1,2,3-triazole derivatives Bioorg. Med. Chem. Lett. 2008, 18, 1195-1198
27. Zhou, Y.; Zhao, Y.; O'Boyle, K. M.; Murphy, P. V. Hybrid angiogenesis inhibitors: synthesis and biological evaluation of bifunctional compounds based on 1-deoxynojirimycin and aryl-1,2,3-triazoles Bioorg. Med. Chem. Lett. 2008, 18, 954-958
28. Ankati, H.; Yang, Y.; Zhu, D.; Biehl, E. R.; Hua, L. Synthesis of optically pure 2-azido-1-arylethanols with isolated enzymes and conversion to triazole-containing β-blocker analogues employing click chemistry J. Org. Chem. 2008, 73, 6433-6436
29. Jantova, S.; Letasiova, S.; Repicky, A.; Ovadekova, R.; Lakatos, B. The effect of 3-(5-nitro-2-thienyl)-9-chloro-5-morpholin-4-yl[1,2,4]triazolo[4,3- c ]quinazoline on cell growth, cell cycle, induction of DNA fragmentation, and activity of caspase 3 in murine leukemia L1210 cells and fibroblast NIH-3T3 cells Cell Biochem. Funct. 2006, 24, 519-530
30. Lauria, A.; Guarcello, A.; Dattolo, G.; Almerico, A. M. Bis-1,2,4-triazolo[4,3- a:3′,4′- c ]quinoxalines of pharmaceutical interest from 1,3-dipolar cycloaddition Tetrahedron Lett. 2008, 49, 1847-1850
31. Kelley, J. L.; Koble, C. S.; Davis, R. G.; McLean, E. W.; Soroko, F. E.; Copper, B. R. 1-(Fluorobenzyl)-4-amino-1 H -1,2,3-triazolo[4,5- c ]pyridines: synthesis and anticonvulsant activity J. Med. Chem. 1995, 38, 4131-4134
32. Genin, M. J.; Allwine, D. A.; Anderson, D. J.; Barbachyn, M. R.; Emmert, D. E.; Garmon, S. A.; Graber, D. R.; Grega, K. C.; Hester, J. B.; Hutchinson, D. K.; Morris, J.; Reischer, R. J.; Ford, C. W.; Zurenko, G. E.; Hamel, J. C.; Schaadt, R. D.; Stapert, D.; Yagi, B. H. Substituent effects on the antibacterial activity of nitrogen-carbon-linked (azolylphenyl)oxazolidinones with expanded activity against the fastidious Gram-negative organisms Haemophilus influenzae and Moraxella catarrhalis J. Med. Chem. 2000, 43, 953-970
33. Buckle, D. R.; Rockell, C. J. M.; Smith, H.; Spicer, B. A. Studies on 1,2,3-triazoles. 13. (Piperazinylalkoxy)-[1]benzopyrano[2,3- d ]-1,2,3-triazol-9(1 H)-ones with combined H 1-antihistamine and mast cell stabilizing properties J. Med. Chem. 1986, 29, 2262-2267
34. Giffin, M. J.; Heaslet, H.; Brik, A.; Lin, Y.-C.; Cauvi, G.; Wong, C.-H.; McRee, D. E.; Elder, J. H.; Stout, C. D.; Torbett, B. E. A copper(I)-catalyzed 1,2,3-triazole azide-alkyne click compound is a potent inhibitor of a multidrug-resistant HIV-1 protease variant J. Med. Chem. 2008, 51, 6263-6270
35. Thomas, A. W. A concise route to triazolobenzodiazepine derivatives via a one-pot alkyne-azide cycloaddition reaction Bioorg. Med. Chem. Lett. 2002, 12, 1881-1893
36. Broggini, G.; Molteni, G.; Terraneo, A.; Zecchi, G. A facile synthesis of flumazenil analogues Tetrahedron 1999, 55, 14803-14806
37. Herzog, B.; Mongiat, S.; Deshayes, C.; Neuhaus, M.; Sommer, K.; Mantler, A. In vivo and in vitro assessment of UVA protection by sunscreen formulations containing either butyl methoxy dibenzoyl methane, methylene bis-benzotriazolyl tetramethylbutylphenol, or microfine ZnO Int. J. Cosmet. Sci. 2002, 24, 170-185
38. Moyal, D. Prevention of ultraviolet-induced skin pigmentation Photodermatol., Photoimmunol. Photomed. 2004, 20, 243-247
39. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective ligation of azides and terminal alkynes Angew. Chem., Int. Ed. 2002, 41, 2596-2599
40. Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Polytriazoles as copper(I)-stabilizing ligands in catalysis Org. Lett. 2004, 6, 2853-2855
41. Feldman, A. K.; Colasson, B.; Fokin, V. V. One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from in situ generated azides Org. Lett. 2004, 6, 3897-3899
42. Zhang, L.; Chen, X.; Xue, P.; Sun, H. H. Y.; Williams, I. D.; Sharpless, K. B.; Fokin, V. V.; Jia, G. Ruthenium-catalyzed cycloaddition of alkynes and organic azides J. Am. Chem. Soc. 2005, 127, 15998-15999
43. Kalisiak, J.; Sharpless, K. B.; Fokin, V. V. General solution to the synthesis of N -2-substituted 1,2,3-triazoles Org. Lett. 2008, 10, 3171-3174
44. Gil, M. V.; Arevalo, M. J.; Lopez, O. Click chemistry-What's in a name? Triazole synthesis and beyond Synthesis 2007, 1589-1620
45. Chuprakov, S.; Chernyak, N.; Dudnik, A. S.; Gevorgyan, V. Direct Pd-catalyzed arylation of 1,2,3-triazoles Org. Lett. 2007, 9, 2333-2336
46. Krivopalov, V. P.; Shkurko, O. P. 1,2,3-Triazole and its derivatives. Development of methods for the formation of the triazole ring Russ. Chem. Rev. 2005, 74, 339-379
47. Wu, W. B.; Huang, J. M. Highly Regioselective C-N bond formation through C-H azolation of indoles promoted by iodine in aqueous media Org. Lett. 2012, 14, 5832-5835
48. Namba, K.; Mera, A.; Osawa, A.; Sakuda, E.; Kitamura, N.; Tanino, K. One-pot synthesis of highly fluorescent 2,5-disubstituted-1,3a,6a- triazapentalene Org. Lett. 2012, 14, 5554-5557
49. Conrad, W. E.; Rodriguez, K. X.; Nguyen, H. H.; Fettinger, J. C.; Haddadin, M. J.; Kurth, M. J. A one-pot-three-step route to triazolotriazepinoindazolones from oxazolino-2 H -indazoles Org. Lett. 2012, 14, 3870-3873
50. Guggenheim, K. G.; Toru, H.; Kurth, M. J. One-pot, two-step cascade synthesis of quinazolinotriazolobenzodiazepines Org. Lett. 2012, 14, 3732-3735
51. Chen, C. Y.; Yang, C. H.; Hu, W. P.; Vandavasi, J. K.; Chung, M. I.; Wang, J. J. Synthesis of fused triazolo[4,5- d ]quinoline/chromene/thiochromene derivatives via palladium catalysis mediated by tetrabutylammonium iodide RSC Adv. 2013, 3, 2710-2719
52. Cai, Q.; Yan, J.; Ding, K. A CuAAC/Ullmann C-C coupling tandem reaction: copper-catalyzed reactions of organic azides with N -(2-Iodoaryl)propiolamides or 2-iodo- N -(prop-2-ynyl)benzenamines Org. Lett. 2012, 14, 3332-3335
53. Arigela, R. K.; Mandadapu, A. K.; Sharma, S. K.; Kumar, B.; Kundu, B. Cascade intermolecular michael addition-intramolecular azide/internal alkyne 1,3-dipolar cycloaddition reaction in one pot Org. Lett. 2012, 14, 1804-1807
54. Yan, J.; Zhou, F.; Qin, D.; Cai, T.; Ding, K.; Cai, Q. Synthesis of [1,2,3]triazolo[1,5- a ]quinoxalin-4(5 H)-ones through copper-catalyzed tandem reactions of N -(2-haloaryl)propiolamides with sodium azide Org. Lett. 2012, 14, 1262-1265
55. Donald, J. R.; Martin, S. F. Synthesis and diversification of 1,2,3-triazole-fused 1,4-benzodiazepine scaffolds Org. Lett. 2011, 13, 852-855
56. Adhikary, N. D.; Chattopadhyay, P. Design and synthesis of 1,2,3-triazole-fused chiral medium-ring benzo-heterocycles, scaffolds mimicking benzolactams J. Org. Chem. 2012, 77, 5399-5405
57. Chowdhury, C.; Mukherjee, S.; Das, B.; Achari, B. Expedient and rapid synthesis of 1,2,3-triazolo[5,1- c ]morpholines through palladium-copper catalysis J. Org. Chem. 2009, 74, 3612-3615
58. Chowdhury, C.; Sasmal, A. P.; Achari, B. An expedient and facile route for the general synthesis of 3-aryl substituted 1,2,3-triazolo[1,5- a ][1,4]benzodiazepin-6-ones and 1,2,3-triazolo[1,5- a ][1,5]benzodiazocin-7-ones Org. Biomol. Chem. 2010, 8, 4971-4977
59. Chowdhury, C.; Mukherjee, S.; Chakraborty, B.; Achari, B. A rapid and facile method for the general synthesis of 3-aryl substituted 4,5,6,7-tetrahydro[1,2,3]triazolo[1,5- a ]pyrazines and their ring fused analogues Org. Biomol. Chem 2011, 9, 5856-5862
60. Declerck, D.; Toupet, L.; Martinez, L.; Lamaty, F. Selective [3 + 2] Huisgen cycloaddition. synthesis of trans-disubstituted triazolodiazepines from aza-Baylis-Hillman adducts J. Org. Chem. 2009, 74, 2004-2007
61. Park, S. P.; Ahn, S. H.; Lee, K. J. 3,5-Disubstituted 6 H -pyrrolo[1,2- c ][1,2,3]triazoles from Morita-Baylis-Hillman adducts of propargyl aldehydes Tetrahedron 2010, 66, 3490-3498
62. Balducci, E.; Bellucci, L.; Petricci, E.; Taddei, M.; Tafi, A. Microwave-assisted intramolecular huisgen cycloaddition of azido alkynes derived from α-amino acids J. Org. Chem. 2009, 74, 1314-1321
63. Jeanmougin, M.; Civatte, J. Dosimetry of solar ultraviolet radiation. Daily and monthly changes in Paris Ann. Dermatol. Venereol. 1987, 114, 671-676
64. Seagrae, J. C.; Burchiel, S. W. Interactions between benzo[ a ]pyrene and UVA light affecting ATP levels, cytoskeletal organization, and resistance to trypsinization Toxicol. Lett. 2000, 117, 11-23
65. Zhong, J. L.; Yiakouvaki, A.; Holley, P.; Tyrrell, R. M.; Pourzand, C. Susceptibility of skin cells to UVA-induced necrotic cell death reflects the intracellular level of labile iron J. Invest. Dermatol. 2004, 123, 771-780
66. Fligiel, S. E.; Varani, J.; Datta, S. C.; Kang, S.; Fisher, G. J.; Voorhees, J. J. Collagen degradation in aged/photodamaged skin in vivo and after exposure to matrix metalloproteinase-1 in vitro J. Invest. Dermatol. 2003, 120, 842-848
67. For review see: Jenkins, G. Molecular mechanisms of skin ageing Mech. Ageing Dev. 2002, 123, 801-810
68. Wlaschek, M.; Briviba, K.; Stricklin, G. P.; Sies, H.; Scharffetter-Kochanek, K. Singlet oxygen may mediate the ultraviolet A-induced synthesis of interstitial collagenase J. Invest. Dermatol. 1995, 104, 194-198
69. Yang, C. C.; Lin, S. D.; Yu, H. S. Effect of growth factors on dermal fibroblast contraction in normal skin and hypertrophic scar J. Dermatol. Sci. 1997, 14, 162-169
70. Kao, C. S.; Yu, H. S. Comparison of the effects of 8-methoxypsoralen (8-MOP) plus UVA (PUVA) on human melanocytes in vitiligo vulgaris and in vitro J. Invest. Dermatol 1992, 98, 734-740
71. Dimri, G. P.; Lee, X.; Basile, G.; Acosta, M.; Scott, G.; roskelley, C.; Medrano, E. E.; Linskens, M.; Rubelj, I.; Pereira-Smith, O. A biomarker that identifies senescent human cells in culture and in aging skin in vivo Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 9363-9367