Synthesis 2014; 46(20): 2763-2770
DOI: 10.1055/s-0034-1378522
paper
© Georg Thieme Verlag Stuttgart · New York

A New Method for Thiomethylation of Hydroxy-1,4-naphthoquinones with N-Acetyl-l-cysteine; First Synthesis of Fibrostatins B, C, and D

Yuri E. Sabutskii
G. B. Elyakov Pacific Institute of Bioorganic Chemistry FEB RAS, Prospect 100 let Vladivostoku 159, 690022 Vladivostok, Russian Federation   Fax: +7(4232)314050   Email: sergpol@piboc.dvo.ru
,
Sergey G. Polonik*
G. B. Elyakov Pacific Institute of Bioorganic Chemistry FEB RAS, Prospect 100 let Vladivostoku 159, 690022 Vladivostok, Russian Federation   Fax: +7(4232)314050   Email: sergpol@piboc.dvo.ru
,
Vladimir A. Denisenko
G. B. Elyakov Pacific Institute of Bioorganic Chemistry FEB RAS, Prospect 100 let Vladivostoku 159, 690022 Vladivostok, Russian Federation   Fax: +7(4232)314050   Email: sergpol@piboc.dvo.ru
,
Pavel S. Dmitrenok
G. B. Elyakov Pacific Institute of Bioorganic Chemistry FEB RAS, Prospect 100 let Vladivostoku 159, 690022 Vladivostok, Russian Federation   Fax: +7(4232)314050   Email: sergpol@piboc.dvo.ru
› Author Affiliations
Further Information

Publication History

Received: 21 April 2014

Accepted after revision: 24 June 2014

Publication Date:
30 July 2014 (online)


Abstract

A series of N-acetyl-S-[(3-hydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl]-l-cysteine conjugates were obtained in good yields by acid-catalyzed condensation of substituted 2-hydroxy-1,4-naphthoquinones with N-acetyl-l-cysteine and paraform­aldehyde. Based on this reaction, a first synthesis of fibrostatins B, C, and D was developed.

Supporting Information

 
  • References

    • 1a Thomson RH. Naturally Occurring Quinones: Recent Advances . 3rd ed. Chapman & Hall; London: 1987
    • 1b Thomson RH. Naturally Occurring Quinones: Recent Advances . 4th ed. Blackie Academic and Professional; London: 1997
    • 2a Bringmann G, Rüdenauer S, Irmer A, Bruhn A, Brun R, Heimberger T, Stühmer T, Bargou R, Chatterjee M. Phytochemistry 2008; 69: 2501
    • 2b Epifano F, Genovese S, Fiorito S, Mathieu V, Kiss R. Phytochem. Rev. 2014; 13: 37
  • 3 Brewer D, Jen WC, Jones GA, Taylor A. Can. J. Microbiol. 1984; 30: 1068
  • 4 Baggish AL, Hill DR. Antimicrob. Agents Chemother. 2002; 46: 1163
    • 5a Belorgey D, Lanfranchi DA, Davioud-Charvet E. Curr. Pharm. Des. 2013; 19: 2512
    • 5b Schuck DC, Ferreira SB, Cruz LN, da Rocha DR, Moraes MS, Nakabashi M, Rosenthal PJ, Ferreira VF, Garcia CR. S. Malar. J. 2013; 12: 234
  • 6 Kumagai Y, Shinkai Y, Miura T, Cho AK. Annu. Rev. Pharmacol. Toxicol. 2012; 52: 221
    • 7a Polonik SG, Prokof’eva NG, Agafonova IG, Uvarova NI. Pharm. Chem. J. 2003; 37: 397
    • 7b Su Y, Xie J, Wang Y, Hu X, Lin X. Eur. J. Med. Chem. 2010; 45: 2713
    • 7c Fedorov SN, Shubina LK, Kuzmich AS, Polonik SG. Open Glycosci. 2011; 4: 1
    • 8a Shreshta-Dawadi PB, Bittner S, Fridkin M, Rahimipour S. Synthesis 1996; 1468
    • 8b Gorohovsky S, Bittner S. Amino Acids 2001; 20: 135
    • 8c Alnabari M, Bittner S. Amino Acids 2001; 20: 381
    • 8d Pachatouridis C, Iakovidou Z, Myoglou E, Mourelatos D, Pantazaki AA, Papageorgiou VP, Kotsis A, Liakopoulou-Kyriakides M. Anti-Cancer Drugs 2002; 13: 367
    • 8e Katritzky AR, Huang L, Sakhuja R. Synthesis 2010; 2011
    • 9a Anufriev VPh, Novikov VL, Maximov OB, Elyakov GB, Levitsky DO, Lebedev AV, Sadretdinov SM, Shvilkin AV, Afonskaya NI, Ruda MYa, Cherpachenko NM. Bioorg. Med. Chem. Lett. 1998; 8: 587
    • 9b Pelageev DN, Dyshlovoy SA, Pokhilo ND, Denisenko VA, Borisova KL, Keller-von Amsberg G, Bokemeyer C, Fedorov SN, Honecker F, Anufriev VPh. Eur. J. Med. Chem. 2014; 77: 139
    • 10a Aoyama T, Zhao W, Kojima F, Muraoka Y, Naganawa H, Takeuchi T, Aoyagi T. J. Antibiot. 1993; 46: 1471
    • 10b Miyata S, Ohhata N, Murai H, Masui Y, Ezaki M, Takase S, Nishikawa M, Kiyoto S, Kohsaka M. J. Antibiot. 1992; 45: 1029
    • 10c Carney JR, Hong S.-T, Gould SJ. Tetrahedron Lett. 1997; 38: 3139
    • 10d Corey EJ, Li W.-DZ. Chem. Pharm. Bull. 1999; 47: 1
    • 10e Kulanthaivel P, Perun Jr T, Belvo M, Strobel R, Poul D, Williams D. J. Antibiot. 1999; 52: 256
    • 10f Fukumoto A, Kim Y.-P, Matsumoto A, Takahashi Y, Shiomi K, Tomoda H, Omura S. J. Antibiot. 2008; 61: 1
    • 10g Nachtigall J, Schneider K, Bratner C, Ball AT, Goodfellow M, Zinecker HP, Imhoff JF, Nicholson J, Irran E, Süssmuth RD, Fiedler HP. J. Antibiot. 2011; 64: 453
    • 10h Wang X, Shaaban KA, Elshahawi SI, Ponomareva LV, Sunkara M, Zhang Y, Copley GC, Hower JC, Morris AJ, Kharel MK, Thorson JS. J. Nat. Prod. 2013; 76: 1441
    • 11a Ishimaru T, Kanamaru T, Ohta K, Okazaki H. J. Antibiot. 1987; 40: 1231
    • 11b Ohta K, Kasahara F, Ishimaru T, Wada Y, Kanamaru T, Okazaki H. J. Antibiot. 1987; 40: 1239
  • 12 Saika S, Ooshima A, Yamanaka O, Okada Y, Tanaka S.-I, Ohnishi Y. Graefe’s Arch. Clin. Exp. Ophthalmol. 1996; 234: 214
  • 13 Kwan HL, Moore HW. J. Korean Chem. Soc. 2003; 47: 47
  • 14 Henke MO, Ratjen F. Paediatr. Respir. Rev. 2007; 8: 24
  • 15 Kanter MZ. Am. J. Health-Syst. Pharm. 2006; 63: 1821
  • 16 Dilger RN, Baker DH. J. Anim. Sci. 2007; 85: 1712
    • 17a Nair V, Treesa PM. Tetrahedron Lett. 2001; 42: 4549
    • 17b da Silva FC, Ferreira SB, Kaiser CR, Pinto AC, Ferreira VF. J. Braz. Chem. Soc. 2009; 20: 1478
  • 18 Sharma A, Santos IO, Gaur P, Ferreira VF, Garcia CR. S, da Rocha DR. Eur. J. Med. Chem. 2013; 59: 48
    • 19a Anufriev VPh, Chizhova AYa, Denisenko VA, Novikov VL. Zh. Org. Khim. 1993; 29: 2008 ; Chem. Abstr. 1994, 120, 255376
    • 19b Pelageev DN, Panchenko MN, Pokhilo ND, Denisenko VA, Anufriev VF. Chem. Nat. Compd. 2008; 44: 719
    • 20a Ichinose K, Ebizuka Y, Sankawa U. Chem. Pharm. Bull. 2001; 49: 192
    • 20b Snyder SA, Tang Z.-Y, Gupta R. J. Am. Chem. Soc. 2009; 131: 5744
    • 21a Fieser LF, Oxford AE. J. Am. Chem. Soc. 1942; 64: 2060
    • 21b Karnojitzki V. Les Peroxides Organiques 1958
    • 22a Singh H, Folk TL, Scheuer P. Tetrahedron 1969; 25: 5301
    • 22b Geber NN, Wieclawek B. J. Org. Chem. 1966; 31: 1496
  • 23 Leffler MT, Hathaway RJ. J. Am. Chem. Soc. 1948; 70: 3222