Home / Publications / An alternative synthesis of the antidepressant Navacaprant

An alternative synthesis of the antidepressant Navacaprant

Yuandong Ma 1, 2
Yuandong Ma
, 
Ruopei Wang 3
Ruopei Wang
, 
Yueqiu Wang 1
Yueqiu Wang
, 
Meihui Zhang 2
Meihui Zhang
, 
Jinhua Dong 2
Jinhua Dong
, 
Dawei Liang 1
Dawei Liang
1 School of Pharmacy and Medical Laboratory Science, Ya’an Polytechnic College, Ya’an 625100, China
2 Key Laboratory of Structure-based Drug Design & Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China
3 Department of Nephrology, Fujian Provincial Clinical Research Center for Glomerular Nephritis, The First Affiliated Hospital of Xiamen University, School of Medicine, Xiamen University, Xiamen 361000, China
10.71267/mencom.7925
Published 2026-03-24
Communication , Volume 36, Issue 3, 326-327
0
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Ma Y. et al. An alternative synthesis of the antidepressant Navacaprant // Mendeleev Communications. 2026. Vol. 36. No. 3. pp. 326-327.
GOST all authors (up to 50) Copy
Ma Y., Wang R., Wang Y., Zhang M., Dong J., Liang D. An alternative synthesis of the antidepressant Navacaprant // Mendeleev Communications. 2026. Vol. 36. No. 3. pp. 326-327.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.71267/mencom.7925
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7925
TI - An alternative synthesis of the antidepressant Navacaprant
T2 - Mendeleev Communications
AU - Ma, Yuandong
AU - Wang, Ruopei
AU - Wang, Yueqiu
AU - Zhang, Meihui
AU - Dong, Jinhua
AU - Liang, Dawei
PY - 2026
DA - 2026/03/24
PB - Mendeleev Communications
SP - 326-327
IS - 3
VL - 36
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2026_Ma,
author = {Yuandong Ma and Ruopei Wang and Yueqiu Wang and Meihui Zhang and Jinhua Dong and Dawei Liang},
title = {An alternative synthesis of the antidepressant Navacaprant},
journal = {Mendeleev Communications},
year = {2026},
volume = {36},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7925},
number = {3},
pages = {326--327},
doi = {10.71267/mencom.7925}
}
MLA
Cite this
MLA Copy
Ma, Yuandong, et al. “An alternative synthesis of the antidepressant Navacaprant.” Mendeleev Communications, vol. 36, no. 3, Mar. 2026, pp. 326-327. https://mendcomm.colab.ws/publications/10.71267/mencom.7925.
Views
2

Keywords

antidepressant
Navacaprant
process optimization
quinolone
Suzuki—Miyaura reaction
synthesis

Abstract

An eight-step synthetic route has been developed for the antidepressant Navacaprant starting from 4-bromo-2-fluoroaniline in 4.7% overall yield, the key step having been the replacement of the 4-positioned bromine atom by the ethyl group employing the Suzuki–Miyaura method. This new protocol offers three key advantages, namely, the use of an inexpensive starting material, independent construction of the quinoline and 1,2,4-oxadiazole moieties, and the introduction of the 4-(tetrahydropyran-4-ylamino)piperidino substituent in a single step.

References

1.
Design and Synthesis of a Novel and Selective Kappa Opioid Receptor (KOR) Antagonist (BTRX-335140)
Guerrero M., Urbano M., Kim E., Gamo A.M., Riley S., Abgaryan L., Leaf N., Van Orden L.J., Brown S.J., Xie J.Y., Porreca F., Cameron M.D., Rosen H., Roberts E.
Journal of Medicinal Chemistry, 2019
2.
The opioid system in depression
Jelen L.A., Stone J.M., Young A.H., Mehta M.A.
Neuroscience and Biobehavioral Reviews, 2022
3.
Opioid receptor modulation of neural circuits in depression: What can be learned from preclinical data?
Puryear C.B., Brooks J., Tan L., Smith K., Li Y., Cunningham J., Todtenkopf M.S., Dean R.L., Sanchez C.
Neuroscience and Biobehavioral Reviews, 2020
5.
A review of kappa opioid receptor antagonists and their clinical trial landscape
Lobe M.M., Verma S., Patil V.M., Iyer M.R.
European Journal of Medicinal Chemistry, 2025
8.
Preclinical and clinical efficacy of kappa opioid receptor antagonists for depression: A systematic review
Wong S., Le G.H., Vasudeva S., Teopiz K.M., Phan L., Meshkat S., Kwan A.T., Rhee T.G., Ho R., Choi H., Cao B., Rosenblat J.D., McIntyre R.S.
Journal of Affective Disorders, 2024
9.
Structure−Reactivity Relationship of Piperidine Nitroxide: Electrochemical, ESR and Computational Studies
Yamasaki T., Mito F., Ito Y., Pandian S., Kinoshita Y., Nakano K., Murugesan R., Sakai K., Utsumi H., Yamada K.
Journal of Organic Chemistry, 2010
10.
Precisely Tailoring the Second Coordination Sphere of a Cobalt Single‐Atom Catalyst for Selective Hydrogenation of Halogenated Nitroarenes
Chen G., Gu J., Gong W., Li J., Li J., Qiu S., Long R., Zhao H., Xiong Y.
Angewandte Chemie - International Edition, 2024
11.
Design, Synthesis, and Biological Evaluation of Aminoindazole Derivatives as Highly Selective Covalent Inhibitors of Wild-Type and Gatekeeper Mutant FGFR4
Shao M., Chen X., Yang F., Song X., Zhou Y., Lin Q., Fu Y., Ortega R., Lin X., Tu Z., Patterson A.V., Smaill J.B., Chen Y., Lu X.
Journal of Medicinal Chemistry, 2022
12.
Access to 2,2‐Halofluorobicyclo[1.1.1] pentanes via Non Ozone‐depleting Ethyl Dihalofluoroacetate
Prakash S., Zhu Z., Tang J., Coe M., Knieb A., Xu Y., Lin D., Zhang C.
Advanced Synthesis and Catalysis, 2025
13.
Structure–activity relationship study of pyrimido[1,2-c][1,3]benzothiazin-6-imine derivatives for potent anti-HIV agents
Mizuhara T., Oishi S., Ohno H., Shimura K., Matsuoka M., Fujii N.
Bioorganic and Medicinal Chemistry, 2012
16.
Synthesis and preliminary biological evaluation of potent and selective 2-(3-alkoxy-1-azetidinyl) quinolines as novel PDE10A inhibitors with improved solubility
Rzasa R.M., Frohn M.J., Andrews K.L., Chmait S., Chen N., Clarine J.G., Davis C., Eastwood H.A., Horne D.B., Hu E., Jones A.D., Kaller M.R., Kunz R.K., Miller S., Monenschein H., et. al.
Bioorganic and Medicinal Chemistry, 2014
17.
Small-Molecule Inhibitors of Histone Acetyltransferase Activity:  Identification and Biological Properties
Mai A., Rotili D., Tarantino D., Ornaghi P., Tosi F., Vicidomini C., Sbardella G., Nebbioso A., Miceli M., Altucci L., Filetici P.
Journal of Medicinal Chemistry, 2006