An improved synthesis of haloacetamidine-based inactivators of protein arginine deiminase 4 (PAD4)

Tetrahedron Letters

Volumn 49, Issue 28, 2008, Pages 4383-4385

  Causey, Corey P ^a   Thompson, Paul R ^a  

^a UNIVERSITY OF SOUTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDINE DERIVATIVE; ANISTREPLASE; HALOACETAMIDINE; PROTEIN ARGININE DEIMINASE 4;

ARTICLE; CHEMICAL STRUCTURE; HYDROLYSIS; RHEUMATOID ARTHRITIS; SYNTHESIS;

EID: 44649174340     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.05.021     Document Type: Article

References (24)

1. Moscarello M.A., Pritzker L., Mastronardi F.G., and Wood D.D. J. Neurochem. 81 (2002) 335-343
2. Ishigami A., Ohsawa T., Hiratsuka M., Taguchi H., Kobayashi S., Saito Y., Murayama S., Asaga H., Toda T., Kimura N., and Maruyama N. J. Neurosci. Res. 80 (2005) 120-128
3. Bhattacharya S.K., Crabb J.S., Bonilha V.L., Gu X., Takahara H., and Crabb J.W. Invest. Ophthalmol. Vis. Sci. 47 (2006) 2508-2514
4. Bhattacharya S.K., Bhat M.B., and Takahara H. Curr. Eye Res. 31 (2006) 1063-1071
5. Chang X., and Han J. Mol. Carcinog. 45 (2006) 183-196
6. Vossenaar E.R., and Van Venrooij W.J. Arthritis Res. Ther. 6 (2004) 107-111
7. Vossenaar E.R., Zendman A.J., van Venrooij W.J., and Pruijn G.J. BioEssays 25 (2003) 1106-1118
8. Suzuki A., Yamada R., Chang X., Tokuhiro S., Sawada T., Suzuki M., Nagasaki M., Nakayama-Hamada M., Kawaida R., Ono M., Ohtsuki M., Furukawa H., Yoshino S., Yukioka M., Tohma S., Matsubara T., Wakitani S., Teshima R., Nishioka Y., Sekine A., Iida A., Takahashi A., Tsunoda T., Nakamura Y., and Yamamoto K. Nat. Genet. 34 (2003) 395-402
9. Kang C.P., Lee H.S., Ju H., Cho H., Kang C., and Bae S.C. Arthritis Rheum. 54 (2006) 90-96
10. Lee Y.H., Rho Y.H., Choi S.J., Ji J.D., and Song G.G. Rheumatol. Int. 27 (2007) 827-833
11. Plenge R.M., Padyukov L., Remmers E.F., Purcell S., Lee A.T., Karlson E.W., Wolfe F., Kastner D.L., Alfredsson L., Altshuler D., Gregersen P.K., Klareskog L., and Rioux J.D. Am. J. Hum. Genet. 77 (2005) 1044-1060
12. Lundberg K., Nijenhuis S., Vossenaar E.R., Palmblad K., van Venrooij W.J., Klareskog L., Zendman A.J., and Harris H.E. Arthritis Res. Ther. 7 (2005) R458-R467
13. Foulquier C., Sebbag M., Clavel C., Chapuy-Regaud S., Al Badine R., Mechin M.C., Vincent C., Nachat R., Yamada M., Takahara H., Simon M., Guerrin M., and Serre G. Arthritis Rheum. 56 (2007) 3541-3553
14. Schellekens G.A., de Jong B.A., van den Hoogen F.H., van de Putte L.B., and van Venrooij W.J. J. Clin. Invest. 101 (1998) 273-281
15. Schellekens G.A., Visser H., de Jong B.A., van den Hoogen F.H., Hazes J.M., Breedveld F.C., and van Venrooij W.J. Arthritis Rheum. 43 (2000) 155-163
16. Machold K.P., Stamm T.A., Nell V.P., Pflugbeil S., Aletaha D., Steiner G., Uffmann M., and Smolen J.S. Rheumatology (Oxford) 46 (2007) 342-349
17. Smolen J.S., and Steiner G. Nat. Rev. Drug. Discov. 2 (2003) 473-488
18. Luo Y., Arita K., Bhatia M., Knuckley B., Lee Y.H., Stallcup M.R., and Thompson P.R. Biochemistry 45 (2006) 11727-11736
19. Luo Y., Knuckley B., Lee Y.H., Stallcup M.R., and Thompson P.R. J. Am. Chem. Soc. 128 (2006) 1092-1093
20. +): calcd 337.1763, observed 337.1761.
21. Bailen M.A., Chinchilla R., Dodsworth D.J., and Nájera C. Tetrahedron Lett. 41 (2000) 2809-9813
22. +): calcd 336.1923, observed 336.1927.
23. +): calcd 236.1399, observed 236.1397.
24. Synthesis of Cl-amidine: N-α-Benzoyl-l-ornithine amide-TFA (247 mg, 0.7 mmol) was dissolved in MeOH (2 mL). Triethyl amine (0.29 mL, 2.1 mmol) and ethyl chloroacetimidate-HCl (221 mg, 1.4 mmol) were added and the mixture stirred overnight. The reaction mixture was quenched with water (5 mL) and acidified with TFA. The product was isolated by RP-HPLC as a white powder. Spectral data were consistent with previous reports.