6-(Methylamino)hexane-1,2,3,4,5-pentanol 4-(((1 S,2 S)-1-hydroxy-2,3- dihydro-1 H,1′ H -[2,2-biinden]-2-yl)methyl)benzoate (PH46A): A novel small molecule with efficacy in murine models of colitis

Journal of Medicinal Chemistry

Volumn 55, Issue 11, 2012, Pages 5497-5505

  Frankish, Neil ^a   Sheridan, Helen ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

6 (METHYLAMINO)HEXANE 1,2,3,4,5 PENTANOL 4 [[(1S,2S) 1 HYDROXY 2,3 DIHYDRO 1H,1'H [2,2 BIINDEN] 2 YL]METHYL]BENZOATE; BENZOIC ACID DERIVATIVE; DEXTRAN SULFATE; INTERLEUKIN 10; PREDNISOLONE; SERUM AMYLOID A; UNCLASSIFIED DRUG;

ANIMAL MODEL; ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; ARTICLE; COLITIS; COLON INJURY; CONTROLLED STUDY; DISEASE EXACERBATION; DOSE RESPONSE; DRUG BIOAVAILABILITY; DRUG EFFICACY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; FEMALE; HISTOLOGY; IN VIVO STUDY; MOUSE; NONHUMAN; PROTEIN BLOOD LEVEL; STEROID THERAPY;

ACUTE DISEASE; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CHRONIC DISEASE; COLITIS; COLON; DISEASE MODELS, ANIMAL; FEMALE; GASTROINTESTINAL HEMORRHAGE; INDANS; INTERLEUKIN-10; INTESTINAL MUCOSA; MICE; MICE, INBRED BALB C; MICE, KNOCKOUT; SERUM AMYLOID A PROTEIN; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; WEIGHT LOSS;

EID: 84862275896     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm300390f     Document Type: Article

References (37)

1. Talley, N. J.; Abreu, M. T.; Achkar, J. P.; Bernstein, C. N.; Dubinsky, M. C.; Hanauer, S. B.; Kane, S. V.; Sandborn, W. J.; Ullman, T. A.; Moayyedi, P. An evidence-based systematic review on medical therapies for inflammatory bowel disease Am. J. Gastroenterol. 2011, 106 (Suppl 1) S2-25 quiz S26.
2. Maloy, K. J.; Powrie, F. Intestinal homeostasis and its breakdown in inflammatory bowel disease Nature 2011, 474, 298-306
3. Mowat, C.; Cole, A.; Windsor, A.; Ahmad, T.; Arnott, I.; Driscoll, R.; Mitton, S.; Orchard, T.; Rutter, M.; Younge, L.; Lees, C.; Ho, G. T.; Satsangi, J.; Bloom, S. Guidelines for the management of inflammatory bowel disease in adults Gut 2011, 60, 571-607
4. Bosani, M.; Ardizzone, S.; Porro, G. B. Biologic targeting in the treatment of inflammatory bowel diseases Biologics 2009, 3, 77-97
5. Melmed, G. Y.; Targan, S. R. Future biologic targets for IBD: potentials and pitfalls Nature Rev. Gastroenterol. Hepatol. 2010, 7, 110-117
6. Cooper, H. S.; Murthy, S. N.; Shah, R. S.; Sedergran, D. J. Clinicopathologic study of dextran sulfate sodium experimental murine colitis Lab. Invest. 1993, 69, 238-249
7. Berg, D. J.; Davidson, N.; Kuhn, R.; Muller, W.; Menon, S.; Holland, G.; Thompson-Snipes, L.; Leach, M. W.; Rennick, D. Enterocolitis and colon cancer in interleukin-10-deficient mice are associated with aberrant cytokine production and CD4(+) TH1-like responses J. Clin. Invest. 1996, 98, 1010-1020
8. Donelly, D. M. X.; Oreilly, J.; Polonsky, J.; Sheidan, M. H. Biosynthesis of Fomajorin-D-Incorporations of [1-C-13]-, [2-C-13]-, and [1,2-C-132]-Acetates J. Chem. Soc., Chem. Commun. 1983, 615-616
9. Donnelly, D. M. X.; Oreilly, J.; Polonsky, J.; Sheridan, M. H. In Vitro Production and Biosynthesis of Fomajorin-D and Fomajorin-S by Fomes-Annosus (Fr) Cooke J. Chem. Soc., Perk. Trans. 1 1987, 1869-1872
10. Jaki, B.; Orjala, J.; Burgi, H. R.; Sticher, O. Biological screening of cyanobacteria for antimicrobial and molluscicidal activity, brine shrimp lethality, and cytotoxicity Pharm. Biol. 1999, 37, 138-143
11. Chen, Y. H.; Chang, F. R.; Lu, M. C.; Hsieh, P. W.; Wu, M. J.; Du, Y. C.; Wu, Y. C. New benzoyl glucosides and cytotoxic pterosin sesquiterpenes from Pteris ensiformis burm Molecules 2008, 13, 255-266
12. Syrchina, A. I.; Semenov, A. A. Natural Indanones Khim. Prir. Soedin. 1982, 3-14
13. Okpekon, T.; Millot, M.; Champy, P.; Gleye, C.; Yolou, S.; Bories, C.; Loiseau, P.; Laurens, A.; Hocquemiller, R. A novel 1-indanone isolated from Uvaria afzelii roots Nat. Prod. Res. 2009, 23, 909-915
14. Ito, T.; Tanaka, T.; Iinuma, M.; Nakaya, K.; Takahashi, Y.; Sawa, R.; Murata, J.; Darnaedi, D. Three new resveratrol oligomers from the stem bark of Vatica pauciflora J. Nat. Prod. 2004, 67, 932-937
15. Vacca, J. P.; Dorsey, B. D.; Schleif, W. A.; Levin, R. B.; McDaniel, S. L.; Darke, P. L.; Zugay, J.; Quintero, J. C.; Blahy, O. M.; Roth, E.; Sardana, V. V.; Schlabach, A. J.; Graham, P. I.; Condra, J. H.; Gotlib, L.; Holloway, M. K.; Lin, J.; Chen, I. W.; Vastag, K.; Ostovic, D.; Anderson, P. S.; Emini, E. A.; Huff, J. R. L-735,524-An Orally Bioavailable Human-Immunodeficiency-Virus Type-1 Protease Inhibitor Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 4096-4100
16. Lin, J. H. Role of pharmacokinetics in the discovery and development of indinavir Adv. Drug. Delivery Rev. 1999, 39, 33-49
17. Jelic, V.; Darreh-Shori, T. Donepezil: A Review of Pharmacological Characteristics and Role in the Management of Alzheimer Disease Clin. Med. Ins. Ther. 2010, 2, 771
18. Oldfield, V.; Keating, G. M.; Perry, C. M. Rasagiline: a review of its use in the management of Parkinson's disease Drugs 2007, 67, 1725-1747
19. Scheper, M. A.; Nikitakis, N. G.; Chaisuparat, R.; Montaner, S.; Sauk, J. J. Sulindac induces apoptosis and inhibits tumor growth in vivo in head and neck squamous cell carcinoma Neoplasia 2007, 9, 192-199
20. Shiff, S. J.; Qiao, L.; Tsai, L. L.; Rigas, B. Sulindac sulfide, an aspirin-like compound, inhibits proliferation, causes cell cycle quiescence, and induces apoptosis in HT-29 colon adenocarcinoma cells J. Clin. Invest. 1995, 96, 491-503
21. Ho, S.-T.; Yang, M.-S.; Wu, T.-S.; Wang, C.-H. Studies on the Taiwan Folk Medicine: III. A Smooth Muscle Relaxant from Onychium siliculosum, Onitin Planta Med. 1985, 148-150
22. Yang, M. S. Studies on the Taiwan folk medicine. VI. Studies on onitin Planta Med. 1986, 25-27
23. Sheridan, H.; Lemon, S.; Frankish, N.; McArdle, P.; Higgins, T.; James, J. P.; Bhandari, P. Synthesis and antispasmodic activity of nature identical substituted indanes and analogs Eur. J. Med. Chem. 1990, 25, 603-608
24. Sheridan, H.; Frankish, N.; Farrell, R. Smooth muscle relaxant activity of pterosin Z and related compounds Planta Med. 1999, 65, 271-272
25. Sheridan, H.; Frankish, N.; Farrell, R. Synthesis and antispasmodic activity of analogues of natural pterosins Eur. J. Med. Chem. 1999, 34, 953-966
26. Farrell, R.; Kelleher, F.; Sheridan, H. Synthesis of fern sesquiterpene pterosin Z via a novel palladium-catalyzed route J. Nat. Prod. 1996, 59, 446-447
27. Frankish, N.; Farrell, R.; Sheridan, H. Investigation into the mast cell stabilizing activity of nature-identical and synthetic indanones J. Pharm. Pharmacol. 2004, 56, 1423-1427
28. Sheridan, H.; Walsh, J. J.; Cogan, C.; Jordan, M.; McCabe, T.; Passante, E.; Frankish, N. H. Diastereoisomers of 2-benzyl-2, 3-dihydro-2-(1 H -inden-2-yl)-1 H -inden-1-ol: potential anti-inflammatory agents Bioorg. Med. Chem. Lett. 2009, 19, 5927-5930
29. Sheridan, H.; Walsh, J. J.; Jordan, M.; Cogan, C.; Frankish, N. A series of 1, 2-coupled Indane dimers with mast cell stabilisation and smooth muscle relaxation properties Eur. J. Med. Chem. 2009, 44, 5018-5022
30. Frankish, N.; Sheridan, H. Unpublished results on Stereochemistry, 2012.
31. Frankish, N.; Sheridan, H. Unpublished Solubility and Pharmacokinetic Studies, 2012.
32. Ford, A. C.; Achkar, J. P.; Khan, K. J.; Kane, S. V.; Talley, N. J.; Marshall, J. K.; Moayyedi, P. Efficacy of 5-aminosalicylates in ulcerative colitis: systematic review and meta-analysis Am. J. Gastroenterol. 2011, 106, 601-616
33. Benchimol, E. I.; Seow, C. H.; Otley, A. R.; Steinhart, A. H. Budesonide for maintenance of remission in Crohn's disease Cochrane DB Syst. Rev. 2009, CD002913
34. Frankish, N.; Sheridan, H. Unpublished Toxicology Observations, 2012.
35. Cummins, E. P.; Seeballuck, F.; Keely, S. J.; Mangan, N. E.; Callanan, J. J.; Fallon, P. G.; Taylor, C. T. The hydroxylase inhibitor dimethyloxalylglycine is protective in a murine model of colitis Gastroenterology 2008, 134, 156-165
36. Axelsson, L. G.; Landstrom, E.; Bylund-Fellenius, A. C. Experimental colitis induced by dextran sulphate sodium in mice: beneficial effects of sulphasalazine and olsalazine Aliment. Pharmacol. Ther. 1998, 12, 925-934
37. L'Heureux, M. C.; Brubaker, P. L. Glucagon-like peptide-2 and common therapeutics in a murine model of ulcerative colitis J. Pharmacol. Exp. Ther. 2003, 306, 347-354