Synthetic modifications of abietane diterpene acids to potent antimicrobial agents

References

• Baldin VP, de Lima Scodro RB, Lopes-Ortiz МA, Aryadne Larissa de Almeida AL, Gazim ZC, Ferarrese L, Faiões VDS, Torres-Santos EC, Claudia Terencio Agostinho Pires CTA, Caleffi-Ferracioli KR, et al. 2018. Anti-Mycobacterium tuberculosis activity of essential oil and 6,7-dehydroroyleanone isolated from leaves of Tetradenia riparia (Hochst.) Codd (Lamiaceae). Phytomedicine. 47:34–39.
   PubMed Web of Science ®Google Scholar
• Blanchet M, Borselli D, Brunel JM. 2016. Polyamine derivatives: a revival of an old neglected scaffold to fight resistant Gram-negative bacteria? Fut Med Chem. 8(9):963–973.
   PubMed Web of Science ®Google Scholar
• Chen GG, Wu HM, Peng CF, Chen IS, Chu SD. 2009. seco-abietane diterpenoids, a phenylethanoid derivative, and antitubercular constituents from Callicarpa pilosissima. J Nat Prod. 72(2):223–228.
   PubMed Web of Science ®Google Scholar
• Cui YM, Liu XL, Zhang WM, Lin HX, Ohwad T, Ido K, Sawada K. 2016. The synthesis and BK channel-opening activity of N-acylaminoalkyloxime derivatives of dehydroabietic acid. Bioorg Med Chem Lett. 26(2):283–287.
   PubMed Web of Science ®Google Scholar
• Fallarero A, Skogman M, Kujala J, Rajaratnam M, Moreira V, Yli-Kauhaluoma J, Vuorela P. 2013. (þ)-Dehydroabietic acid, an abietane-type diterpene, inhibits Staphylococcus aureus biofilms in vitro. IJMS. 14(6):12054–e12072.
   Google Scholar
• Ferreira ML, Gonçalves RSB, Cardoso LNF, Kaiser CR, Candéa ALP, Henriques MGMO, Lourenço MCS, Bezerra FAFM, Souza MVN. 2010. Synthesis and antitubercular activity of heteroaromatic isonicotinoyl and 7-chloro-4-quinolinyl hydrazone derivatives. Sci World J. 10:1347–1355.
   Web of Science ®Google Scholar
• Flekhter OB, Tret'yakova EV, Makara NS, Gabdrakhmanova SF, Baschenko NZh, Galin FZ, Zarudii FS, Tolstikov GA. 2003. Synthesis and antiulcer activity of quinopimaric acid derivatives. Russ. Pharm. Chem. J. 37(3):142–144.
   Google Scholar
• Gonzalez MA. 2014. Synthetic derivatives of aromatic abietane diterpenoids and their biological activities. Eur J Med Chem. 87(24):834–842.
   PubMedGoogle Scholar
• González MA, Correa-Royero J, Agudelo L, Mesa A, Betancur-Galvis L. 2009. Synthesis and biological evaluation of abietic acid derivatives. Eur J Med Chem. 44(6):2468–2472.
   PubMed Web of Science ®Google Scholar
• Hou W, Zhang G, Luo Z, Li D, Ruan H, Ruan BH, Su L, Xu H. 2017. Identification of a diverse synthetic abietane diterpenoid library and insight into the structure-activity relationships for antibacterial activity. Bioorg Med Chem Lett. 27(24):5382–5386.
   PubMed Web of Science ®Google Scholar
• Kang S, Zhang J, Yuan Y. 2018. Abietic acid attenuates IL-1β-induced inflammation in human osteoarthritis chondrocytes. Int Immunopharmacol. 64:110–115.
   PubMed Web of Science ®Google Scholar
• Kazakova OB, Giniyatullina GV, Mustafin AG, Babkov DA, Sokolova EV, AA, Spasov AA. 2020. Evaluation of cytotoxicity and α-glucosidase inhibitory activity of amide and polyamino-derivatives of lupane triterpenoids. Molecules. 25(20):4833.
   PubMed Web of Science ®Google Scholar
• Kazakova OB, Medvedeva NI, Samoilova IA, Baikova IP, Tolstikov GA, Kataev VE, Mironov VF. 2011. Conjugates of several lupane, oleanane, and ursane triterpenoids with the antituberculosis drug isoniazid and pyridinecarboxaldehydes. Chem Nat Compd. 47(5):752–758.
   Web of Science ®Google Scholar
• Kazakova OB, Medvedeva NI, Smirnova IE, Lopatina TV, Veselovsky AV. 2021. The introduction of hydrazone, hydrazide, or azepane moieties to the triterpenoid core enhances an activity against M. tuberculosis. Med Chem. 17(2):134–145.
   PubMed Web of Science ®Google Scholar
• Kazakova OB, Tretyakova EV, Kukovinets OS, Abdrakhmanova AR, Kabalnova NN, Kazakov DV, Tolstikov GA, Gubaidullin AT. 2010a. Synthesis of nontrivial quinopimaric acid derivatives by oxidation with dimethyldioxirane. Tetrahedron Lett. 51(14):1832–1835.
   Web of Science ®Google Scholar
• Kazakova OB, Tret'yakova EV, Kukovinets OS, Tolstikov GA, Nazyrov TI, Chudov IV, Ismagilova AF. 2010b. Synthesis and pharmacological activity of amides and ozonolysis product of maleopimaric acid. Russ J Bioorg Chem. 36:832–840.
   Web of Science ®Google Scholar
• Kazakova OB, Tret’yakova EV, Smirnova IE, Spirikhin LV, Tolstikov GA, Chudov IV, Bazekin GV, Ismagilova AF. 2010c. The synthesis and anti-inflammatory activity of quinopimaric acid derivatives. Russ J Bioorg Chem. 36(2):257–262.
   Web of Science ®Google Scholar
• Manner S, Vahermo M, Skogman ME, Krogerus S, Vuorela PM, Yli-Kauhaluoma J, Fallarero A, Moreira VM. 2015. New derivatives of dehydroabietic acid target planktonic and biofilm bacteria in Staphylococcus aureus and effectively disrupt bacterial membrane integrity. Eur J Med Chem. 102:68–79.
   PubMed Web of Science ®Google Scholar
• Rijo P, Simoes MF, Francisco AP, Rojas R, Gilman RH, Vaisberg AJ, Rodriguez B, Moiteiro C. 2010. Antimycobacterial Metabolites from Plectranthus: Royleanone Derivatives against Mycobacterium tuberculosis Strains. Chem Biodivers. 7(4):922–932.
   PubMed Web of Science ®Google Scholar
• Sepúlveda B, Astudillo L, Rodríguez JA, Yáñez T, Theoduloz C, Schmeda-Hirschmann G. 2005. Gastroprotective and cytotoxic effect of dehydroabietic acid derivatives. Pharmacol Res. 52(5):429–437.
   PubMed Web of Science ®Google Scholar
• Smirnova IE, Tret’yakova EV, Flekhter OB, Spirikhin LV, Galin FZ, Tolstikov GA, Starikova ZA, Korlyukov AA. 2008. Synthesis, structure, and acylation of dihydroquinopimaric acid hydroxyl derivatives. Russ J Org Chem. 44(11):1598–1605.
   Web of Science ®Google Scholar
• Smirnova IE, Kazakova OB, Loesche A, Hoenke S, Csuk R. 2020. Evaluation of cholinesterase inhibitory activity and cytotoxicity of synthetic derivatives of di- and triterpene metabolites from Pinus silvestris and Dipterocarpus alatus resins. Med Chem Res. doi:10.1007/s00044-020-02566-9.
   Web of Science ®Google Scholar
• Smirnova IE, Tret'yakova EV, Kazakova OB, Starikova ZA, Fedyanin IV. 2009. Molecular and crystal structure of a new compound methyl-18R-13-isopropyl-10a,7-dimethyl-4-oxo- 1-oxahexacyclo. 12.4.0.0 5a,4a.0 13,12 0 1,1a.0 10a,6a]heneicosane7-Carboxylate. J Struct Chem. 50:378–380.
   Web of Science ®Google Scholar
• Spivak AY, Khalitova RR, Nedopekina DA, Gubaidullin RR. 2020. Antimicrobial properties of amine- and guanidine-functionalized derivatives of betulinic, ursolic and oleanolic acids: Synthesis and structure/activity evaluation. Steroids. 154:108530.
   PubMed Web of Science ®Google Scholar
• Sychrová A, Koláriková I, Žemlička M, Šmejkal K. 2020. Natural compounds with dual antimicrobial and anti-inflammatory effects. Phytochem Rev. 19(6):1471–1502.
   Web of Science ®Google Scholar
• Tretyakova EV, Smirnova IE, Kazakova OB, Tolstikov GA, Yavorskaya NP, Golubeva IS, Pugacheva RB, Apryshko GN, Poroikov VV. 2014. Synthesis and anticancer activity of quinopimaric and maleopimaric acids’ derivatives. Bioorg Med Chem. 22(22):6481–6489.
   PubMed Web of Science ®Google Scholar
• Tret'yakova EV, Salimova EV, Parfenova LV. 2020. Synthesis, modification, and biological activity of propargylated methyl dihydroquinopimarates. Nat Prod Res. 12 :1–8.
   PubMed Web of Science ®Google Scholar
• Tret’yakova EV, Zakirova EF, Salimova EV, Kukovinets OS, Odinokov VN, Parfenova LV. 2018. Convenient one-pot synthesis of resin acid Mannich bases as novel anticancer and antifungal agents. Med Chem Res. 27(9):2199–2213.
   Web of Science ®Google Scholar
• Xu HT, Liu LL, Fan XT, Zhang GJ, Li YC, Jiang B. 2017. Identification of a diverse synthetic abietane diterpenoid library for anticancer activity. Bioorg Med Chem Lett. 27(3):505–510.
   PubMed Web of Science ®Google Scholar
• Zhang WM, Yang T, Pan XY, Liu XL, Lin HX, Gao ZB, Yang CG, Cui YM. 2017. The synthesis and antistaphylococcal activity of dehydroabietic acid derivatives: modifications at C12 and C7. Eur J Med Chem. 127:917–927.
   PubMed Web of Science ®Google Scholar
• Zhang YY, Zhou CH. 2011. Synthesis and activities of naphthalimide azoles as a new type of antibacterial and antifungal agents. Bioorg Med Chem Lett. 21(14):4349–4352.
   PubMed Web of Science ®Google Scholar