Synthesis and RNase A inhibition study of C2-symmetric bis-isochromenyl sulfones

Tetrahedron Letters

Volumn 51, Issue 21, 2010, Pages 2828-2831

  Mitra, Tapobrata ^a   Dutta, Sansa ^a   Basak, Amit ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BIS ISOCHROMENE DERIVATIVE; BIS PROPARGYL SULFONE DERIVATIVE; CHROMENE DERIVATIVE; ISOCOUMARIN DERIVATIVE; RIBONUCLEASE A; SULFONE DERIVATIVE; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; ENZYME INHIBITION; ENZYME SYNTHESIS; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 77950931823     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.03.075     Document Type: Article

References (41)

1. Larsen T.O., and Breinholt J. J. Nat. Prod. 62 (1999) 1182
2. Lee, J. J.; Kim, H.-S.; Lee, J.-H.; Hong, Y.-S.; Park, Y. J. PCT Int. Appl. WO 2000075124.
3. Wang B., Li M., Xu S., Song H., and Wang B. Synthesis (2007) 1643
4. Alper P.B., and Nguyen K.T. J. Org. Chem. 68 (2003) 2051
5. Hudson A.R., Roach S.L., Higuchi R.I., Phillips D.P., Bissonnette R.P., Lamph J., Yen W.W., Li Y., Adams M.E., Valdez L.J., Vassar A., Cuervo C., Kallel E.A., Gharbaoui C.J., Mais D.E., Miner J.N., Marschke K.B., Rungta D., Negro-Vilar A., and Zhi L. J. Med. Chem. 50 (2007) 4699
6. Faggi C., Garcia-Valverde M., Marcaccini S., and Menchi G. Org. Lett. 12 (2010) 788
7. Soulie, P.; Gamelin, E.; Eder, J. Proc. Am. Soc. Clin. Oncol. 2003, Abstract No. 777.
8. Bonate, P.; Eder, J.; Soulie, P. Proc. Am. Soc. Clin. Oncol. 2003, Abstract No. 537.
9. Kawano T., Agata N., Kharbanda S., Avigan D., and Kufe D. Cancer Chemother. Pharmacol. 59 (2007) 329
10. Liu G., Zhou Y., Ye D., Zhang D., Ding X., Jiang H., and Liu H. Adv. Synth. Catal. 351 (2009) 2605
11. Bian M., Yao W., Ding H., and Ma C. J. Org. Chem. 75 (2010) 269
12. Varela-Fernández A., González-Rodri{dotless}́guez C., Varela J.A., Castedo L., and Saá C. Org. Lett. 11 (2009) 5350
13. Mellons J.W. Nat. Med. 2 (1996) 274
14. Petit S.C., Simsic J., Michael S.F., and Swanstrom R. Perspect. Drug Discovery Des. 1 (1993) 69
15. Darke P.L., and Huff J.R. Adv. Pharmacol. 25 (1994) 399
16. Back T.G. Tetrahedron 57 (2001) 5263
17. Basak A., and Khamrai U.K. Tetrahedron Lett. 36 (1995) 7913
18. Basak A., Mandal S., Das A.K., and Bertolasi V. Bioorg. Med. Chem. Lett. 12 (2002) 873
19. Basak A., Khamrai U.K., and Mallik U. Chem. Commun. (1996) 749
20. Garratt P.J., and Neoh S.B. J. Org. Chem. 44 (1979) 2667
21. Cheng Y.S.P., Garratt P.J., Neoh S.B., and Rumjanek V.H. Isr. J. Chem. 26 (1985) 101
22. Braverman S., Duar Y., and Segev D. Tetrahedron Lett. 17 (1979) 3181
23. Zafrani Y., Gottlieb H.E., Sprecher M., and Braverman S. J. Org. Chem. 70 (2005) 10166
24. Sonogashira K., Tohoda Y., and Hagihara N. Tetrahedron Lett. 16 (1975) 4467
25. Takahashi S., Kuroyama Y., Sonogashira K., and Hagihara N. Synthesis (1980) 627
26. Jones G.B., Weight J.M., Hynd G., Wyatt J.K., Rarner P.M., Huber R.S., Li A., Kilgore M.W., Sticca R.P., and Pollenz R.S. J. Org. Chem. 67 (2002) 5727
27. Basak A., Bag S.S., and Das A.K. Eur. J. Org. Chem. 7 (2005) 1239
28. The absence of any NOE between the H-8 and the Hα or the methyl in the alanine based isochromene 7a suggested a Z-configuration of the imine (for NOESY spectrum, see Supplementary data).
29. Lee J.H., Park Y.J., Kim H.S., Hong Y.S., Kim K.-W., and Lee J.J. J. Antibiot. 54 (2001) 463
30. Nakashima T., Hirano S., Agata N., Kumagai H., Isshiki K., Yoshioka T., Ishizuka M., Maeda K., and Takeuchi T. J. Antibiot. (Tokyo) 52 (1999) 426
31. Agata N., Nogi H., Milhollen M., Kharbanda S., and Kufe D. Cancer Res. 64 (2004) 8512
32. Agata N., Hirano S., Abe C., Nakashima T., Tsuchiya A., Kumagai H., Isshiki K., Yoshioka T., Ishizuka M., and Takeuchi T. Res. Commun. Mol. Pathol. Pharmacol. 108 (2000) 297
33. Raines R.T. Chem. Rev. 98 (1998) 1045
34. Vallee B.L., and Riordan J.F. Cell. Mol. Life Sci. 53 (1997) 803
35. Folkman J., and Klagsbrun M. Science 235 (1987) 442
36. Riordan J.F. In: D'Alessio G., and Riordan J.F. (Eds). Ribonucleases: Structure and Function (1997), Academic Press, New York 445
37. Fett J.W., Strydom D.J., Lobb R.R., Alderman E.M., Bethune J.L., Riordan J.F., and Vallee B.L. Biochemistry 24 (1985) 5480
38. Maity T.K., De S., Dasgupta S., and Pathak T. Bioorg. Med. Chem. 14 (2006) 1221
39. Incubation condition: The incubation was done at rt in MeOH for 2 h. For Figure 3a, a 1.15 mM stock solution of each of 7d, 8 and 9 was used. For Figure 3b, the concentrations of the compounds 7d and 8 are the concentrations of the stock (effective concentrations are three times less). The stock concentrations of the RNA and RNase A are 10 mg/mL and 0.8 μM, respectively.
40. Mitra T., Das S., and Basak A. Tetrahedron Lett. 50 (2009) 5846
41. + 383.0590 found 383.0596.