4-Alkyl-3-azidomethyl-2-ethoxy-2,5-dihydro-5H-1,2-oxaphosphole 2-Oxides: Synthesis and 1,3-Cycloaddition

Abstract

Starting from phosphorylated allenes, a three-steps synthesis of a new class of organic azides with a 1,2-oxaphospholene carbon skeleton has been developed. The series of obtained 4-alkyl-3-azidomethyl-2-ethoxy-2,5-dihydro-5H-1,2-oxaphosphole 2-oxides were utilized in the 1,3-cycloaddition with alkyl 2-[1-(propyn-2-yl)-1H-indol-3-yl]-2-oxoacetates for the synthesis of conjugates, which are potentially active cytostatics.

Key words

allenes - azides - 1,2-oxaphosphole 2-oxides - 1,2,3-triazoles - indolylglyoxyl derivatives

Publication History

Received: 18 June 2021

Accepted after revision: 17 September 2021

Article published online:
21 October 2021

• References

• 1 Colvin OM. Curr. Pharm. Des. 1999; 5: 555
• 2 Wardle NJ, Bligh SW. A, Hudson HR. Curr. Org. Chem. 2005; 9: 1803
• 3 Kalir A, Kalir HH. In The Chemistry of Organophosphorus Compounds, Vol. 4, Chap. 9. Hartley FR. Wiley; Chichester: 1996: 774
• 4a Kafarski P, Lejczak B. Curr. Med. Chem. Anticancer Agents 2001; 1: 301
• 4b Varga PR, Keglevich G. Molecules 2021; 26: 2511
• 5 Stresing V, Daubine F, Benzaid I, Wonkkonen H, Clezardin P. Cancer Lett. 2007; 257: 16
• 6 Hollis LS, Miller AV, Amundsen AR, Schurig JE, Stern EW. J. Med. Chem. 1990; 33: 105
• 7 Bloemink MJ, Diederen JJ. H, Dorenbos JP, Heetebrij RJ, Keppler BK, Reedjik J. Eur. J. Inorg. Chem. 1999; 1655
• 8a Hudson HR, Keglevich G. Phosphorus Sulfur Silicon Relat Elem. 2008; 183: 2256
• 8b Balam SK, Harinath JS, Krishnammagari SK, Gajjala RR, Polireddy K, Baki VB, Gu W, Valasani KR, Avula VK. R, Vallela S, Zyryanov GV, Pasupuleti VR, Cirandur SR. ACS Omega 2021; 6: 11375
• 8c Drabowicz J, Krasowska D, Łopusiński A, Heugebaert TS. A, Stevens CV. In Phosphorus Heterocycles II. Topics in Heterocyclic Chemistry, Vol. 21. Bansal R. Springer; Berlin: 2010: 103
• 8d Enchev DD. In Phosphorus Heterocycles II. Topics in Heterocyclic Chemistry, Vol. 21. Bansal RK. Springer-Verlag; Berlin: 2010: 23
• 9a Kalcheva A, Dragoeva A, Kalchev K, Enchev D. Genet. Mol. Biol. 2009; 32: 389
• 9b Koleva V, Dragoeva A, Draganov M, Melendez-Alafort L, Rosato A, Uzunov N, Enchev D. Genetika 2014; 46: 1
• 9c Enchev DD, Koleva VP, Dragoeva AP, Behchet-Ibryam LB, Mihaylov MN, Uzunov NM, Melendez-Alafort LA, Brel V. J. Appl. Pharm. Sci. 2018; 8: 080
• 9d Berger O, Montchamp J-L. Beilstein J. Org. Chem. 2014; 10: 732
• 9e Virieux D, Volle J.-N, Pirat J.-L. ARKIVOC 2012; (iv): 264
• 10a Ishikawa T, Nishigaya K, Uchikoshi H, Chen IS. J. Nat. Prod. 1998; 61: 534
• 10b Guo YW, Gavagnin M, Mollo E, Trivellone E, Cimino G. J. Nat. Prod. 1999; 62: 1194
• 10c Brown SP, Goodwin NC, MacMillan DW. C. J. Am. Chem. Soc. 2003; 125: 1192
• 10d Bagal SK, Adlington RM, Baldwin JE, Marquez R. J. Org. Chem. 2004; 69: 9100
• 10e Lee SS, Lin YS, Chen CK. J. Nat. Prod. 2009; 72: 1249
• 10f Liu XQ, Gao WY, Guo YQ, Zhang TJ, Yan LL. Chin. Chem. Lett. 2007; 18: 1075
• 11a Lattmann E, Ayuko WO, Kinchinaton D, Langley CA, Singh H, Karimi L, Tisdale MJ. J. J. Pharm. Pharmacol. 2003; 55: 129
• 11b Braun M, Hohmann A, Rahematpura J, Behne C, Grimme S. Chem. Eur. J. 2004; 10: 4584
• 11c Xavier NM, Rauter AP. Carbohydr. Res. 2008; 343: 1523
• 11d Pimentel-Elardo SM, Kozytska S, Bugni TS, Ireland SM, Moll H, Hentschel U. Mar. Drugs 2010; 8: 373
• 12a Kupchan SM, Fessler DC, Eakin MA, Giacobbe TJ. Science 1970; 168: 37
• 12b Kupchan SM, Eakin MA, Thomas AM. J. Med. Chem. 1971; 14: 1147
• 12c Bourguignon JJ, Schoenfelder A, Schmitt M, Wermuth CG, Hechler V, Charlier B, Maitre M. J. Med. Chem. 1988; 31: 893
• 13 Kanno TY. N, Sensiate LA, de Paula NA, Salles MJ. S. Braz. J. Pharm. Sci. 2009; 45: 313
• 14a Tam RC, Ramasamy K, Bard J, Pai B, Lim C, Averett DR. Antimicrob. Agents Chemother. 2000; 44: 1276
• 14b Kamiya NJ. J. Antimicrob. Chemother. 2003; 51: 1085
• 14c Pescovitz MD. Future Virol. 2008; 3: 435
• 15a Brel VK. Synthesis 2002; 1829
• 15b Brel VK. Synthesis 2009; 3405
• 15c Brel VK, Artyushin OI, Chuprov-Netochin RN, Leonov SV, Semenova MN, Semenov VV. Bioorg. Med. Chem. Lett. 2020; 30: 127635
• 16a Ignat’ev VM, Angelov Ch, Ionin BI, Petrov AA. Zh. Obshch. Khim. 1975; 45: 2342
• 16b Angelov Ch. Phosphorus Sulfur Relat. Elem. 1983; 15: 177
• 16c Alabugin IV, Brel VK, Zyk NV, Zefirov NS. Izv. Akad. Nauk. Ser. Khim. 1996; 779
• 16d Hwan J, Lee BS, Lee SY, Lee H.-Y. Tetrahedron Lett. 2003; 44: 5811
• 16e Lv Y, Hu G, Ma D, Liu L, Gao Y, Zhao Y. J. Org. Chem. 2015; 80: 6908
• 16f Brel VK, Abramkin EV. Mendeleev Commun. 2002; 12: 64
• 16g Ismailov IE, Ivanov IK, Christov VCh. Molecules 2014; 19: 11056
• 17 Brel VK. Synthesis 2007; 2674
• 18a Bacher G, Nickel B, Emig P, Vanhoefer U, Seeber S, Shandra A, Klenner T, Beckers T. Cancer Res. 2001; 61: 392
• 18b Kapoor S, Srivastava S, Panda D. Sci. Rep. 2018; 8: 12363
• 18c Colley HE, Muthana M, Danson SJ. J. Med. Chem. 2015; 58: 9309
• 18d Wienecke A, Bacher G. Cancer Res. 2009; 69: 171
• 19 Semenova MN, Kiselyov AS, Titov IY, Raishtat MM, Molodtsov M, Grishchuk E, Spiridoniv I, Semenov VV. Chem. Biol. Drug Des. 2007; 70: 485
• 20 Han L, Liu C, Zhang W, Shi X, You S. Chem. Commun. 2014; 50: 1231
• 21 Brel VK, Abramkin EV, Martynov IV, Ionin BI. Zh. Obshch. Khim. 1989; 59: 2142 ; Chem. Abstr. 1990, 112, 179192v