Home / Publications / New abiraterone analogue with atypical position of N-heterocyclic substituent: synthesis, crystal structure and CYP17A1/CYP3A4 binding affinity

New abiraterone analogue with atypical position of N-heterocyclic substituent: synthesis, crystal structure and CYP17A1/CYP3A4 binding affinity

Evgeniya Vladimirovna Nurieva 1
Evgeniya Vladimirovna Nurieva
, 
Elena V Britikova 2
Elena V Britikova
, 
Anna V Sydoriuk 1
Anna V Sydoriuk
,  , 
Alexandra Valerievna Mamaeva 1
Alexandra Valerievna Mamaeva
, 
Nikolay A. Zefirov 3
Nikolay A. Zefirov
, 
Anastasiya V. Zazdravnykh 1
Anastasiya V. Zazdravnykh
, 
Victor Aleksandrovich Tafeenko 1
Victor Aleksandrovich Tafeenko
, 
Èduard Valeryevich Bocharov 4
Èduard Valeryevich Bocharov
, 
Vladimir V Britikov 2
Vladimir V Britikov
,  , 
Ol'ga Nikolaevna Zefirova 1
Ol'ga Nikolaevna Zefirova
10.71267/mencom.7900
Published 2026-02-03
Communication , Volume 36, Issue 2, 138-141
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Nurieva E. V. et al. New abiraterone analogue with atypical position of N-heterocyclic substituent: synthesis, crystal structure and CYP17A1/CYP3A4 binding affinity // Mendeleev Communications. 2026. Vol. 36. No. 2. pp. 138-141.
GOST all authors (up to 50) Copy
Nurieva E. V., Britikova E. V., Sydoriuk A. V., Antonenko T. A., Mamaeva A. V., Zefirov N. A., Zazdravnykh A. V., Tafeenko V. A., Bocharov È. V., Britikov V. V., Milaeva E. R., Zefirova O. N. New abiraterone analogue with atypical position of N-heterocyclic substituent: synthesis, crystal structure and CYP17A1/CYP3A4 binding affinity // Mendeleev Communications. 2026. Vol. 36. No. 2. pp. 138-141.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.71267/mencom.7900
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7900
TI - New abiraterone analogue with atypical position of N-heterocyclic substituent: synthesis, crystal structure and CYP17A1/CYP3A4 binding affinity
T2 - Mendeleev Communications
AU - Nurieva, Evgeniya Vladimirovna
AU - Britikova, Elena V
AU - Sydoriuk, Anna V
AU - Antonenko, Taisiya Alekseevna
AU - Mamaeva, Alexandra Valerievna
AU - Zefirov, Nikolay A.
AU - Zazdravnykh, Anastasiya V.
AU - Tafeenko, Victor Aleksandrovich
AU - Bocharov, Èduard Valeryevich
AU - Britikov, Vladimir V
AU - Milaeva, Elena Rudol'fovna
AU - Zefirova, Ol'ga Nikolaevna
PY - 2026
DA - 2026/02/03
PB - Mendeleev Communications
SP - 138-141
IS - 2
VL - 36
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2026_Nurieva,
author = {Evgeniya Vladimirovna Nurieva and Elena V Britikova and Anna V Sydoriuk and Taisiya Alekseevna Antonenko and Alexandra Valerievna Mamaeva and Nikolay A. Zefirov and Anastasiya V. Zazdravnykh and Victor Aleksandrovich Tafeenko and Èduard Valeryevich Bocharov and Vladimir V Britikov and Elena Rudol'fovna Milaeva and Ol'ga Nikolaevna Zefirova},
title = {New abiraterone analogue with atypical position of N-heterocyclic substituent: synthesis, crystal structure and CYP17A1/CYP3A4 binding affinity},
journal = {Mendeleev Communications},
year = {2026},
volume = {36},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7900},
number = {2},
pages = {138--141},
doi = {10.71267/mencom.7900}
}
MLA
Cite this
MLA Copy
Nurieva, Evgeniya Vladimirovna, et al. “New abiraterone analogue with atypical position of N-heterocyclic substituent: synthesis, crystal structure and CYP17A1/CYP3A4 binding affinity.” Mendeleev Communications, vol. 36, no. 2, Feb. 2026, pp. 138-141. https://mendcomm.colab.ws/publications/10.71267/mencom.7900.
Views
2

Keywords

abiraterone
cytochrome P450 17A1 inhibitors
prostate cancer
rearrangement of steroid core
steroids
X-ray analysis

Abstract

Atypical steroid-like analogue of abiraterone, an inhibitor of androgen biosynthesis, was synthesized and characterized by X-ray diffraction analysis. The in vitro study of the compound by differential spectrophotometric titration revealed its ability to bind to truncated CYP17A1 (∆2–19 variant) in a type II fashion through nitrogen coordination with lower affinity than that of abiraterone, but still in nanomolar concentration range (KD ≈ 187 nm). The significant spectral response (∆Amax) value suggests that the new compound effectively targets the conformational ensemble of CYP17A1 accessible for ligand binding.

Funders

Russian Science Foundation
22-63-00016
Belarusian Republican Foundation
X23RNF-091

References

2.
Non-steroidal CYP17A1 Inhibitors: Discovery and Assessment
Wróbel T.M., Jørgensen F.S., Pandey A.V., Grudzińska A., Sharma K., Yakubu J., Björkling F.
Journal of Medicinal Chemistry, 2023
3.
Abiraterone and Galeterone, Powerful Tools Against Prostate Cancer: Present and Perspective
Kuzminac I.Z., Nikolić A.R., Savić M.P., Ajduković J.J.
Pharmaceutics, 2024
4.
Abiraterone acetate and its use in the treatment of metastatic prostate cancer: a review
Caffo O., Veccia A., Kinspergher S., Maines F.
Future Oncology, 2018
6.
Fe(iii)-Catalyzed synthesis of steroidal imidazoheterocycles as potent antiproliferative agents
Samanta S., Ghosh A.K., Ghosh S., Ilina A.A., Volkova Y.A., Zavarzin I.V., Scherbakov A.M., Salnikova D.I., Dzichenka Y.U., Sachenko A.B., Shirinian V.Z., Hajra A.
Organic and Biomolecular Chemistry, 2020
8.
Slow-, Tight-Binding Inhibition of CYP17A1 by Abiraterone Redefines Its Kinetic Selectivity and Dosing Regimen
Cheong E.J., Nair P.C., Neo R.W., Tu H.T., Lin F., Chiong E., Esuvaranathan K., Fan H., Szmulewitz R.Z., Peer C.J., Figg W.D., Chai C.L., Miners J.O., Chan E.C.
Journal of Pharmacology and Experimental Therapeutics, 2020
10.
Identification of Novel Steroidal Androgen Receptor Degrading Agents Inspired by Galeterone 3β-Imidazole Carbamate
Purushottamachar P., Kwegyir-Afful A.K., Martin M.S., Ramamurthy V.P., Ramalingam S., Njar V.C.
ACS Medicinal Chemistry Letters, 2016
11.
Synthesis of the Anti-Prostate Cancer Drug Abiraterone Acetate
Li J., Ma S., Tang H., Xu F.
Heterocycles, 2018
12.
Nurieva E.V., Kravtsova O.Y., Sydoriuk A.V., Britikova E.V., Britikov V.V., Zefirov N.A., Milaeva E.R., Zefirova O.N.
Mendeleev Communications, 2024
13.
Deeva O.A., Pantileev A.S., Kravtsova O.Y., Nikolaev S.V., Zefirov N.A., Povarnina P.Y., Antipova T.A., Gudasheva T.A., Dorofeev V.L.
Mendeleev Communications, 2024
14.
Efficient Synthesis of IPL576,092:  A Novel Anti-Asthma Agent
Shen Y., Burgoyne D.L.
Journal of Organic Chemistry, 2002
15.
Novel Dehydroepiandrosterone Derivatives with Antiapoptotic, Neuroprotective Activity
Calogeropoulou T., Avlonitis N., Minas V., Alexi X., Pantzou A., Charalampopoulos I., Zervou M., Vergou V., Katsanou E.S., Lazaridis I., Alexis M.N., Gravanis A.
Journal of Medicinal Chemistry, 2009
16.
Design, synthesis, and pharmacological evaluation of JDTic analogs to examine the significance of replacement of the 3-hydroxyphenyl group with pyridine or thiophene bioisosteres
Kormos C.M., Gichinga M.G., Runyon S.P., Thomas J.B., Mascarella S.W., Decker A.M., Navarro H.A., Carroll F.I.
Bioorganic and Medicinal Chemistry, 2016
18.
Synthesis and antitumor activity of novel steroidal imidazolium salt derivatives
Deng G., Zhou B., Wang J., Chen Z., Gong L., Gong Y., Wu D., Li Y., Zhang H., Yang X.
European Journal of Medicinal Chemistry, 2019
19.
Neighboring Carbon and Hydrogen. XVI. 1,3-Interactions and Homoallylic Resonance
Simonetta M., Winstein S.
Journal of the American Chemical Society, 1954
20.
WinGXandORTEP for Windows: an update
Farrugia L.J.
Journal of Applied Crystallography, 2012
21.
A short history of SHELX
Sheldrick G.M.
Acta Crystallographica Section A Foundations of Crystallography, 2007
22.
Mercury: visualization and analysis of crystal structures
Macrae C.F., Edgington P.R., McCabe P., Pidcock E., Shields G.P., Taylor R., Towler M., van de Streek J.
Journal of Applied Crystallography, 2006
24.
Substrate interaction with cytochrome P-450.
Schenkman J.B., Sligar S.G., Cinti D.L.
Pharmacology and Therapeutics, 1981