Synthesis, pharmacology, crystal properties, and quantitative solvation studies from a drug transport perspective for three new 1,2,4-thiadiazoles

Journal of Pharmaceutical Sciences

Volumn 99, Issue 9, 2010, Pages 3754-3768

  Perlovich, German L ^a,b   Volkova, Tatyana V ^a   Proshin, Alexey N ^b   Sergeev, Dmitriy Yu ^b   Bui, Cong Trinh ^a   Petrova, Ludmila N ^b   Bachurin, Sergey O ^b  

^a INSTITUTE OF SOLUTION CHEMISTRY   (Russian Federation)

^b INSTITUTE OF PHYSIOLOGICALLY ACTIVE COMPOUNDS   (Russian Federation)

Author keywords

1,2,4 thiadiazoles; Biological activity; Crystal structure; Distribution; Solubility; Solvation; Sublimation thermodynamics; Transfer process

Indexed keywords

1 [(5 PHENYLAMINO) 1,2,4 THIADIAZOL 3 YL] PROPAN 2 OL; 1 [(5, 4 TOLYLAMINO) 1,2,4 THIADIAZOL 3 YL] PROPAN 2 OL; 1 [5 (4 ETHOXYPHENYLAMINO) 1,2,4 THIADIAZOL 3 YL] PROPAN 2 OL; 1,2,4 THIADIAZOLE DERIVATIVE; CALCIUM; HEXANE; OCTANOL; SOLVENT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONFORMATION; CRYSTAL STRUCTURE; DRUG SOLUBILITY; DRUG SYNTHESIS; DRUG TRANSPORT; ENTHALPY; ENTROPY; HYDROGEN BOND; NEWBORN; NONHUMAN; RAT; SOLVATION; TEMPERATURE DEPENDENCE; THERMODYNAMICS; VAPOR PRESSURE; X RAY DIFFRACTION;

EID: 77956383433     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22143     Document Type: Article

References (32)

1. Castro A, Castaño T, Encinas A, Porcal W, Gil C. 2006. Advances in the synthesis and recent therapeutic applications of 1,2,4-thiadiazole heterocycles. Bioorg Med Chem 14:1644-1652.
2. Martínez A, Alonso M, Castro A, Pérez C, Moreno FJ. 2002. First non-ATP competitive glycogen synthase kinase 3 β (GSK-3β) inhibitors: Thiadiazolidinones (TDZD) as potential drugs for the treatment of Alzheimer's disease. J Med Chem 45:1292-1299.
3. Martínez A, Alonso D, Castro A, Arán VJ, Cardelus I, Baños JE, Badía A. 1999. Synthesis and potential muscarinic receptor binding and antioxidant properties of 3-(Thiazolyl)pyridine 1-Oxides compounds. Arch Pharm Pharm Med Chem 332:191-194.
4. Martínez A, Fernández E, Castro A, Conde S, Rodríguez-Franco I, Baños JE, Badía AE. 2000. N-Benzylpiperidine derivatives of 1,2,4-thiadiazolidinone as new acetylcholinesterase inhibitors. Eur J Med Chem 35:913-922.
5. Macleod AM, Baker R, Freedman SB, Patel S, Merchant KJ, Roe M, Saunders J. 1990. Synthesis and muscarinic activities of 1,2,4-Thiadiazoles. J Med Chem 33:2052-2059.
6. Alonso M, Martínez A. 2004. GSK-3 inhibitors: Discoveries and developments. Curr Med Chem 11:753-761.
7. Lanzafame A, Christopoulos A. 2004. Investigation of the interaction of a putative allosteric modulator, N-(2,3-Diphenyl-1,2,4-thiadiazole-5-(2H)- ylidene) methanamine hydrobromide (SCH-202676), with M1 muscarinic acetylcholine receptors. J Pharmacol Exp Ther 308:830-837.
8. Fawzi AB, Macdonald D, Benbow LL, Smith-Torhan A, Zhang HT, Weig BC, Ho G, Tulshian D, Linder ME, Graziano MP. 2001. SCH-202676: An allosteric modulator of both agonist and antagonist binding to G protein-coupled receptors. Mol Pharmacol 59:30-37.
9. Gao ZG, Gross AS, Jacobson KA. 2004. Effects of the allosteric modulator SCH-202676 on adenosine and P2Y receptors. Life Sci 74:3173-3180.
10. Unangst PC, Shrum GP, Connor DT, Dyer RD, Schrier DJ. 1992. Novel 1,2,4-oxadiazeles and 1,2,4-thiadiazoles as dual 5-lipoxygenase and cyclooxygenase inhibitors. J Med Chem 35:3691-3698.
11. Decking UKM, Hartmann M, Rose H, Bruckner R, Meil J, Schrader J. 1998. Cardioprotective actions of KC 12291 I. Inhibition of voltage-gated Na+ channels in ischemia delays myocardial Na+ overload. Naunyn-Schmiedeberg's. Arch Pharmacol 358:547-553.
12. Hartmann M, Decking UKM, Schrader J. 1998. Cardioprotective actions of KC 12291 II. Delaying Na+ overload in ischemia improves cardiac function and energy status in reperfusion. Naunyn-Schmiedeberg's. Arch Pharmacol 358:554-560.
13. Miyazaki S, Okazaki K, Tsuji M, Yamaguchi K. 2004. Pharmacodynamics of S-3578, a novel cephem, in murine lung and systemic infection models. Antimicrob Agents Chemother 48:378-383. (Pubitemid 38141690)
14. Yoshizawa H, Kubota T, Itani H, Ishitobi H, Miwa H, Nishitani Y. 2004. New broad-spectrum parenteral cephalosporins exhibiting potent activity against both methicillin-resistant Staphylococcus aureus (MRSA) and Pseudomonas aeruginosa. Part 2: Synthesis and structure-activity relationships in the S-3578 series. Bioorg Med Chem 12:4211-4219.
15. Lazarev AI, Kharlamov IP, Yakovlev PY, Yakovleva EF. 1976. Hand-book of chem-analyst. Moscow: Metallurgiya. pp. 132-135.
16. Guillory JK. 1999. Polymorphism in pharmaceutical solids, edited by H.G. Brittain. New York: Marcel Dekker, Inc. pp. 183-226.
17. Enraf-Nonius. 1989. CAD-4 Software. Version 5.0. Delft, the Netherlands: Enraf-Nonius.
18. Sheldrick GM. 1997. SHELXL97 and SHELXS97. Germany: University of Göttingen.
19. Pascual-Ahuir JL, Silla E. 1990. GEPOL: An improved description of molecular surfaces. I. Building the spherical surface set. J Comp Chem 11:1047.
20. Perlovich GL, Bauer-Brandl A. 2004. Solvation of drugs as a key for understanding partitioning and passive transport exemplified by NSAIDs. Current Drug Deliv 1:213-226.
21. Zielenkiewicz W, Perlovich G, Wszelaka-Rylik M. 1999. The vapour pressure and the enthalpy of sublimation determination by inert gas flow method. J Thermal Anal Calorimetry 57:225-234.
22. Cox JD, Pilcher G. 1970. Thermochemistry of organic and organometallic compounds. London: Academic Press.
23. Chickos JS, Acree WE, Jr. 2002. Enthalpies of sublimation of organic and organometallic compounds. 1910-2001. J Phys Chem Ref Data 31:537-698.
24. Vivona N, Cusmano G, Macaluso G. 1977. Mononuclear heterocyclic rearrangements. Part 11. Rearrangements of 1,2,4-oxadiazoles, isoxazoles, and 1,2,5-oxadiazoles involving a sulphur atom. J Chem Soc Perkin Trans 1:1616-1619.
25. Etter MC. 1990. Encoding and decoding hydrogen-bond patterns of organic compounds. Acc Chem Res 23:120-126.
26. Bernstein J, Davis RE, Shimoni L, Chang N-L. 1995. Patterns in hydrogen bonding: Functionality and graph set analysis in crystals. Angew Chem Int Ed Engl 34:1555-1573.
27. Perlovich GL, Volkova TV, Manin AN, Bauer-Brandl A. 2008. Influence of position and size of substituents on the mechanism of partitioning: A thermodynamic study on acetaminophens, hydroxybenzoic acids, and parabens. AAPS PharmSciTech 9:205-216.
28. Perlovich GL, Surov AO, Bauer-Brandl A. 2007. Thermodynamic properties of Flufenamic and Niflumic acids - Specific and non-specific interactions in solution and in crystal lattices, mechanism of solvation, partitioning and distribution. J Pharm Biomed Anal 45:679-687.
29. Li ZJ, Ojala WH, Grant DJW. 2001. Molecular modeling study of chiral drug crystals: Lattice energy calculations. J Pharm Sci 90:1523-1539.
30. Seiler P. 1974. Interconversion of lipophilicities from hydrocarbon/ water systems into the octanol/water system. Eur JMed Chem 9:473-479.
31. Young RC, Mitchell RC, Brown TH, Ganellin CR, Griffiths R, Jones M, Rana KK, Saunders D, Smith IR, Sore NE, Wilks TJ. 1988. Development of a new physicochemical model for brain penetration and its application to the design of centrally acting H2 receptor histamine antagonists. J Med Chem 31:656-671.
32. Toulmin AJ, Wood M, Kenny PW. 2008. Toward prediction of alkane/water partition coefficients. J Med Chem 51:3720-3730.