Везде

RAS Chemistry & Material ScienceЖурнал общей химии Russian Journal of General Chemistry

  • ISSN (Print) 0044-460X
  • ISSN (Online) 3034-5596

7-(2-aryl-1-cyanovinyl)-1,2,3,4-tetrahydropyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles: synthesis and biological activity

You can
PII
10.31857/S0044460X23060069-1
DOI
10.31857/S0044460X23060069
Publication type
Article
Status
Published
Authors
P. G Dahno
  • Affiliation:
    Kuban State University
    North Caucasus Federal University
M. V. Kozlova
  • Affiliation: North Caucasus Federal University
Volume/ Edition
Volume 93 / Issue number 6
Pages
876-890
Abstract
A new method was proposed for the preparation of 5-amino-3-(cyanomethyl)-1 H -pyrazole-4-carbonitrile by reacting the potassium salt of malononitrile dimer with hydrazinium sulfate. The reaction of 5-amino-3(cyanomethyl)-1 H -pyrazole-4-carbonitrile with aromatic aldehydes in the presence of catalytic amounts of morpholine leads to the formation of Knoevenagel condensation products. Aminomethylation of the resulting ( Z )-5amino-3-(2-aryl-1-cyanovinyl)-1 H -pyrazole-4-carbonitriles with primary aromatic amines and excess aqueous HCHO in refluxing DMF leads to the formation of 7-(2-aryl-1-cyanovinyl)-1,2,3,4-tetrahydropyrazolo[1,5- a ][1,3,5]triazine-8-carbonitriles. Bioavailability parameters were studied in silico , and possible protein targets were predicted by protein-ligand docking. In an in vitro experiment on cultures of E. coli , S. aureus and B. pumilis , 5-amino-3-(cyanomethyl)-1 H -pyrazole-4-carbonitrile does not show any noticeable antibacterial effect. At the same time, three compounds of the pyrazolo[1,5- a ][1,3,5]triazine series showed a pronounced antidote effect against the herbicide 2,4-D on sunflower seedlings in a laboratory experiment, for one compound a noticeable growth-stimulating effect was noted.
Keywords
5-амино-3-цианометил-1H-пиразол-4-карбонитрил реакция Манниха пиразоло[1,5-a][1,3,5]триазины антидотная активность ростостимулирующее действие
Date of publication
17.09.2025
Year of publication
2025
Number of purchasers
0
Views
16

References

  1. 1. Kobe J., Robins R. K., O'Brien D.E. // J. Heterocycl. Chem. 1974. Vol. 11. N 2. P. 199. doi 10.1002/jhet.5570110217
  2. 2. Kobe J., O'Brien D.E., Robins R.K., Novinson T. // J. Heterocycl. Chem. 1974. Vol. 11. N 6. P. 991. doi 10.1002/jhet.5570110625
  3. 3. Dolzhenko A., Dolzhenko A., Chui W.-K. // Heterocycles. 2008. Vol. 75. N 7. P. 1575. doi 10.3987/REV-08-629
  4. 4. Cascioferro S., Parrino B., Spanò V., Carbone A., Montalbano A., Barraja P., Diana P., Cirrincione G. // Eur. J. Med. Chem. 2017. Vol. 142. P. 523. doi 10.1016/j.ejmech.2017.09.035
  5. 5. Alizadeh S.R., Ebrahimzadeh M.A. // Eur. J. Med. Chem. 2021. Vol. 223. Paper N 113537. doi 10.1016/j.ejmech.2021.113537
  6. 6. Sun L., Bera H., Chui W.-K. // Eur. J. Med. Chem. 2013. Vol. 65. P. 1. doi 10.1016/j.ejmech.2013.03.063
  7. 7. Sun L., Li J., Bera H., Dolzhenko A.V., Chiu G.N.C., Chui W.-K. // Eur. J. Med. Chem. 2013. Vol. 70. P. 400. doi 10.1016/j.ejmech.2013.10.022
  8. 8. Bera H., Lee M.H., Sun L., Dolzhenko A.V., Chui W.-K. // Bioorg. Chem. 2013. Vol. 50. P. 34. doi 10.1016/j.bioorg.2013.07.004
  9. 9. Nie Z., Perretta C., Erickson P., Margosiak S., Almassy R., Lu J., Averill A., Yager K.M., Chu S. // Bioorg. Med. Chem. Lett. 2007. Vol. 17. N 15. P. 4191. doi 10.1016/j.bmcl.2007.05.041
  10. 10. Nie Z., Perretta C., Erickson P., Margosiak S., Lu J., Averill A., Almassy R., Chu, S. // Bioorg. Med. Chem. Lett. 2008. Vol. 18. N 2. P. 619. doi 10.1016/j.bmcl.2007.11.074
  11. 11. El Hage K., Piquemal J.-P., Oumata N., Meijer L., Galons H., Gresh N. // ACS Omega. 2017. Vol. 2. N 7. P. 3467. doi 10.1021/acsomega.7b00471
  12. 12. Laufer R., Li S.-W., Liu Y., Ng G., Lang Y., Feher M., Brokx R., Beletskaya I., Hodgson R., Mao G., Plotnikova O., Awrey D.E., Mason J.M., Wei X., Chi-Chia Lin D., Che Y., Kiarash R., Madeira B., Fletcher G.C., Mak T.W., Bray M.R., Pauls H.W. // Bioorg. Med. Chem. Lett. 2016. Vol. 26. N 15. P. 3562. doi 10.1016/j.bmcl.2016.06.021
  13. 13. Smolnikov S.A., Gorgopina E.V., Lezhnyova V.R., Ong G.E.-T., Chui W.-K., Dolzhenko A.V. // Molbank. 2017. Vol. 2017. N 4. Paper M970. doi 10.3390/M970
  14. 14. Popowycz F., Fournet G., Schneider C., Bettayeb K., Ferandin Y., Lamigeon C., Tirado O.M., MateoLozano S., Notario V., Colas P., Bernard P., Meijer L., Joseph B. // J. Med. Chem. 2009. Vol. 52. N 3. P. 655. doi 10.1021/jm801340z
  15. 15. Oudah K.H., Najm M.A.A., Samir N., Serya R.A.T., Abouzid K.A.M. // Bioorg. Chem. 2019. Vol. 92. Paper N 103239. doi 10.1016/j.bioorg.2019.103239
  16. 16. Kawanishi E., Tanaka Y., Matsumura T., Kado Y., Taniuchi H. Pat. WO 2013027794 (2013); Chem. Abstr. 2013. Vol. 158. N 349780.
  17. 17. Raboisson P., Schultz D., Muller C., Reimund J.M., Pinna G., Mathieu R., Bernard P., Do Q.T., Desjarlais R.L., Justiano H., Lugnier C., Bourguignon J.J. // Eur. J. Med. Chem. 2008. Vol. 43. N 4. P. 816. doi 10.1016/j.ejmech.2007.05.016
  18. 18. Nishimura M., Yamaoka K., Naito S., Nakagawa T. // Biol. Pharm. Bull. 1997. Vol. 20. N 12. P. 1285. doi 10.1248/bpb.20.1285
  19. 19. Naito S., Nishimura M., Jin Y. // Eur. J. Drug Metab. Pharmacokinet. 1999. Vol. 24. N 3. P. 279. doi 10.1007/BF03190032
  20. 20. Naito S., Nishimura M., Nogawa H. // J. Pharm. Pharmacol. 1999. Vol. 51. N 3. P. 347. doi 10.1211/0022357991772358
  21. 21. Naito S., Nishimura M. // Xenobiotica. 2000. Vol. 30. N 1. P. 103. doi 10.1080/004982500237866
  22. 22. Naito S., Nishimura M., Tamao Y. // J. Pharm. Pharmacol. 2000. Vol. 52. N 2. P. 173. doi 10.1211/0022357001773823
  23. 23. He L., Gilligan P.J., Zaczek R., Fitzgerald L.W., McElroy J., Shen H.S., Saye J.A., Kalin N.H., Shelton S., Christ D., Trainor G., Hartig P. // J. Med. Chem. 2000. Vol. 43. N 3. P. 449. doi 10.1021/jm9904351
  24. 24. Gilligan P.J., Folmer B.K., Hartz R.A., Koch S., Nanda K.K., Andreuski S., Fitzgerald L., Miller K., Marshall W.J. // Bioorg. Med. Chem. 2003. Vol. 11. N 18. P. 4093. doi 10.1016/s0968-0896(03)00398-5
  25. 25. Nielsen D.M., Carey G.J., Gold L.H. // Eur. J. Pharmacol. 2004. Vol. 499. N 1-2. P. 135. doi 10.1016/j.ejphar.2004.07.091
  26. 26. Gilligan P.J., He L., Clarke T., Tivitmahaisoon P., Lelas S., Li Y.W., Heman K., Fitzgerald L., Miller K., Zhang G., Marshall A., Krause C., McElroy J., Ward K., Shen H., Wong H., Grossman S., Nemeth G., Zaczek R., Arneric S.P., Hartig P., Robertson D., Trainor G. // J. Med. Chem. 2009. Vol. 52. N 9. P. 3073. doi 10.1021/jm9000242
  27. 27. Gilligan P.J., Clarke T., He L., Lelas S., Li Y.W., Heman K., Fitzgerald L., Miller K., Zhang G., Marshall A., Krause C., McElroy J.F., Ward K., Zeller K., Wong H., Bai S., Saye J., Grossman S., Zaczek R., Arneric S.P., Hartig P., Robertson D., Trainor G. // J. Med. Chem. 2009. Vol. 52. N 9. P. 3084. doi 10.1021/jm900025h
  28. 28. Saito T., Obitsu T., Minamoto C., Sugiura T., Matsumura N., Ueno S., Kishi A., Katsumata S., Nakai H., Toda M. // Bioorg. Med. Chem. 2011. Vol. 19. N 20. P. 5955. doi 10.1016/j.bmc.2011.08.055
  29. 29. Popowycz F., Schneider C., Debonis S., Skoufias D.A., Kozielski F., Galmarini C.M., Joseph B. // Bioorg. Med. Chem. 2009. Vol. 17. N 9. P. 3471. doi 10.1016/j.bmc.2009.03.007
  30. 30. Wagner J.D., Zhang L., Kavanagh K., Ward G.M., Chin J.E., Hadcock J.R., Auerbach B.J., Harwood H.J., Jr. // J. Pharmacol. Exp. Therap. 2010. Vol. 335. N 1. P. 103. doi 10.1124/jpet.110.168187
  31. 31. Hadcock J.R., Carpino P.A., Iredale P.A., Dow R.L., Gautreau D., Thiede L., Kelly-Sullivan D., Lizano J.S., Liu X., Van Deusen J., Ward K.M., O'Connor R.E., Black S.C., Griffith D.A., Scott D.O. // BMC Pharmacol. 2010. Vol. 10. P. 9. doi 10.1186/1471-2210-10-9
  32. 32. Hutterer C., Eickhoff J., Milbradt J., Korn K., Zeitträger I., Bahsi H., Wagner S., Zischinsky G., Wolf A., Degenhart C., Unger A., Baumann M., Klebl B., Marschall M. // Antimicrob Agents Chemother. 2015. Vol. 59. N 4. P. 2062. doi 10.1128/AAC.04534-14
  33. 33. Vishwakarma J.N., Mofizuddin M., Ila H., Junjappa H. // J. Heterocycl. Chem. 1988. Vol. 25. N 5. P. 1387. doi 10.1002/jhet.5570250523
  34. 34. Dutta M.C., Chanda K., Helissey P., Vishwakarma J.N. // J. Heterocycl. Chem. 2005. Vol. 42. N 5. P. 975. doi 10.1002/jhet.5570420535
  35. 35. Taylor E.C., Hartke K.S. // J. Am. Chem. Soc. 1959. Vol. 81. N 10. P. 2452. doi 10.1021/ja01519a044
  36. 36. Доценко В.В., Кривоколыско С.Г., Семенова А.М. // ХГС. 2018. Т. 54. № 11. С. 989
  37. 37. Dotsenko V.V., Krivokolysko S.G., Semenova A.M. // Chem. Heterocycl. Compd. 2018. Vol. 54. N. 11. P. 989. doi 10.1007/s10593-018-2383-y
  38. 38. Elghandour A.H.H., Elmoghayar M.R.H., Ramiz M.M.M. // J. Prakt. Chem. 1988. Vol. 330. N 4. P. 657. doi 10.1002/prac.19883300424
  39. 39. Naik N.S., Shastri L.A., Shastri S.L., Chougala B.M., Shaikh F., Madar J.M., Kulkarni R.C., Dodamani S., Jalalpure S., Joshi S.D., Sunagar V. // ChemistrySelect. 2019. Vol. 4. N 1. P. 285. doi 10.1002/slct.201802927
  40. 40. Abdelmoniem A.M., Ghozlan S.A., Abdelmoniem D.M., Elwahy A.H., Abdelhamid I.A. // J. Heterocycl. Chem. 2018. Vol. 55. N 12. P. 2792. doi 10.1002/jhet.3346
  41. 41. Metwally N.H., Abdallah M.A., Almabrook S.A. // J. Heterocycl. Chem. 2017. Vol. 54. N 1. P. 347. doi 10.1002/jhet.2590
  42. 42. Hassan M.I., Hassane A.M.A. // Egypt. J. Chem. 2019. Vol. 62. Pt 1. P. 103. doi 10.21608/EJCHEM.2019.14725.1907
  43. 43. Golubev P., Karpova E.A., Pankova A.S., Sorokina M., Kuznetsov M.A. // J. Org. Chem. 2016. Vol. 81. N 22. P. 11268. doi 10.1021/acs.joc.6b02217
  44. 44. Metwally N.H., Mohamed M.S., Deeb E.A. // Res. Chem. Intermed. 2021. Vol. 47. N 12. P. 5027. doi 10.1007/s11164-021-04564-x
  45. 45. Семенова А.М., Гаджиахмедова Я.Р., Беспалов А.В., Доценко В.В., Аксенов Н.А., Аксенова И.В. // ЖОХ. 2022. Т. 92. № 3. С. 415
  46. 46. Semenova A.M., Gadzhiakhmedova Y.R., Bespalov A.V., Dotsenko V.V., Aksenov N.A., Aksenova I.V. // Russ. J. Gen. Chem. 2022. Vol. 92. N 3. P. 367. doi 10.1134/S1070363222030057
  47. 47. El-Qaliei M.I., Mousa S.A., Nasr H.M., Ìshak E.A. // Egypt. J. Chem. 2022. Vol. 65. N 11. P. 331. doi 10.21608/EJCHEM.2022.124950.5560
  48. 48. Wichmann J., Woltering T.J. Pat. WO 2005040171 (2005).
  49. 49. Cohen C. Pat. DE 2900288 (1979). Germany // С. А. 1979. Vol. 91. 157770.
  50. 50. Elkholy A., Al-Qalaf F., Elnagdi M.H. // Arkivoc. 2008. Vol. xiv. P. 124. doi 10.3998/ark.5550190.0009.e14
  51. 51. Kankanala J., Marchand C., Abdelmalak M., Aihara H., Pommier Y., Wang Z. // J. Med. Chem. 2016. Vol. 59.N 6. P. 2734. doi: 10.1021/acs.jmedchem.5b01973
  52. 52. Metwally N.H., Deeb E.A. // Synth. Commun. 2018. Vol. 48. N 13. P. 1614. doi 10.1080/00397911.2018.1457162
  53. 53. Ragab E.A., Metwally N.H., Mohamed M.S. // Synth. Commun. 2017. Vol. 47. N 2. P. 148. doi 10.1080/00397911.2016.1257722
  54. 54. Bulychev Y.N., Korbukh I.A., Preobrazhenskaya M.N. // Chem. Heterocycl. Compd. 1981. Vol. 17. N 4. P. 392. doi 10.1007/BF00503346
  55. 55. Elnagdi M.H., El-Moghayar M.R., Fleita D.H., Hafez E.A., Fahmy S.M. // J. Org. Chem. 1976. Vol. 41. N 24. P. 3781. doi 10.1021/jo00886a002
  56. 56. Elnagdi M.H., Erian A.W. // Lieb. Ann. Chem. 1990. Vol. 1990. N 12. P. 1215. doi 10.1002/jlac.1990199001219
  57. 57. Kolosov M.A., Beloborodov D.A., Orlov V.D., Dotsenko V.V. // New J. Chem. 2016. Vol. 40. N 9. P. 7573. doi 10.1039/c6nj00336b
  58. 58. Семенова А.М., Оганесян Р.В., Доценко В.В., Чигорина Е.А., Аксенов Н.А., Аксенова И.В., Нетреба Е.Е. // ЖОХ. 2019. Т. 89. № 1. С. 25
  59. 59. Semenova A.M., Oganesyan R.V., Dotsenko V.V., Chigorina E.A., Aksenov N.A., Aksenova I.V., Netreba E.E. // Russ. J. Gen. Chem. 2019. Vol. 89. N 1. P. 19. doi 10.1134/S1070363219010043
  60. 60. Ledenyova I.V., Didenko V.V., Dotsenko V.V., Shikhaliev K.S. // Tetrahedron Lett. 2014. Vol. 55. N 6. P. 1239. doi 10.1016/j.tetlet.2014.01.010
  61. 61. Sato T. // J. Org. Chem. 1959. Vol. 24. N 7. P. 963. doi 10.1021/jo01089a019
  62. 62. Carboni R.A., Coffman D.D., Howard E.G. // J. Am. Chem. Soc. 1958. Vol. 80. N 11. P. 2838. doi 10.1021/ja01544a061
  63. 63. Mittelbach M. // Monatsh. Chem. 1985. Vol. 116. N 5. P. 689. doi 10.1007/BF00798796
  64. 64. Lipinski C.A., Lombardo F., Dominy B.W., Feeney P.J. // Adv. Drug. Delivery Rev. 1997. Vol. 23. N 1-3. P. 4. doi 10.1016/S0169-409X(96)00423-1
  65. 65. Lipinski C.A. // Drug Discov. Today: Technologies. 2004. Vol. 1. N 4. P. 337. doi 10.1016/j.ddtec.2004.11.007
  66. 66. Lipinski C.A., Lombardo F., Dominy B.W., Feeney P.J. // Adv. Drug. Delivery Rev. 2012. Vol. 64. Suppl. P. 4. doi 10.1016/j.addr.2012.09.019
  67. 67. Sander T. OSIRIS Property Explorer. Idorsia Pharmaceuticals Ltd, Switzerland. http://www.organic-chemistry.org/prog/peo
  68. 68. Cheng F., Li W., Zhou Y., Shen J., Wu Z., Liu G., Lee P.W., Tang Y. // J. Chem. Inf. Model. 2012. Vol. 52. N 11. P. 3099. doi 10.1021/ci300367a
  69. 69. Yang J., Kwon S., Bae S.H., Park K.M., Yoon C., Lee J.H., Seok C. // J. Chem. Inf. Model. 2020. Vol. 60. N 6. P. 3246. doi 10.1021/acs.jcim.0c00104
  70. 70. GalaxyWEB. A web server for protein structure prediction, refinement, and related methods. Computational Biology Lab, Department of Chemistry, Seoul National University, S. Korea. http://galaxy.seoklab.org/index.html
  71. 71. Ko J., Park H., Heo L., Seok C. // Nucleic Acids Res. 2012. Vol. 40. N W1. P. W294. doi 10.1093/nar/gks493
  72. 72. Pettersen E.F., Goddard T.D., Huang C.C., Couch G.S., Greenblatt D.M., Meng E.C., Ferrin T.E. // J. Сomput. Chem. 2004. Vol. 25. N 13. P. 1605. doi 10.1002/jcc.20084
  73. 73. UCSF Chimera. Visualization system for exploratory research and analysis developed by the Resource for Biocomputing, Visualization, and Informatics at the University of California, San Francisco, US. https://www.rbvi.ucsf.edu/chimera
  74. 74. Стрелков В.Д., Дядюченко Л.В., Дмитриева И.Г. Синтез новых гербицидных антидотов для подсолнечника. Краснодар: Просвещение-Юг, 2014. С. 6.
  75. 75. Hoffmann O.L. // Weeds. 1962. Vol. 10. N 4. P. 322. doi 10.2307/4040837
  76. 76. Davies J., Caseley J.C. // Pesticide Sci. 1999. Vol. 55. N 11. P. 1043. doi 10.1002/(SICI)1096-9063(199911)55:113.0.CO
  77. 77. 2-L
  78. 78. Abu-Qare A.W., Duncan H.J. // Chemosphere. 2002. Vol. 48. N 9. P. 965. doi 10.1016/S0045-6535(02)00185-6
  79. 79. Jia L., Jin X.Y., Zhao L.X., Fu Y., Ye F. // J. Agric. Food Chem. 2022. Vol. 70. N 18. P. 5499. doi 10.1021/acs.jafc.2c01565
  80. 80. Шаповалов А.А., Жирмунская Н.М., Зубкова Н.Ф., Овсянникова Т.В., Грузинская Н.А. Методические рекомендации по проведению лабораторных испытаний синтетических регуляторов роста растений. Черкассы: НИИТЭХИМ, 1990.
  81. 81. Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A.K., Puschmann H. // J. Appl. Cryst. 2009. Vol. 42. P. 339. doi 10.1107/S0021889808042726
  82. 82. Sheldrick G.M. // Acta Crystallogr. (A). 2008. Vol. 64. P. 112. doi 10.1107/S0108767307043930
  83. 83. Sheldrick G.M. // Acta Crystallogr. (C). 2015. Vol. 71. P. 3. doi 10.1107/S2053229614024218
QR
Translate

Индексирование

Scopus

Scopus

Scopus

Crossref

Scopus

Higher Attestation Commission

At the Ministry of Education and Science of the Russian Federation

Scopus

Scientific Electronic Library