The Synthesis and the Mechanism of a Five-Membered Ring Formation Between an Isothiocyanate and an Amide Leading to the Yield of Enzalutamide Anticancer Api; a Joint Experimental and Theoretical Study

The Synthesis and the Mechanism of a Five-Membered Ring Formation Between an Isothiocyanate and an Amide Leading to the Yield of Enzalutamide Anticancer Api; a Joint Experimental and Theoretical Study Publisher

Siadati SA¹ ; Davoudi S¹ ; Soheilizad M¹ ; Firoozpour L^{1, 2} ; Payab M¹ ; Bagherpour S¹ ; Kolivand S¹

Show Affiliations

1. Department of Research & Development, Parsian Pharmaceutical Technology Company, Alborz, Iran
2. Department of Medicinal Chemistry, Faculty of Pharmacy and The Institute of Pharmaceutical Sciences (TIPS), Tehran University of Medical Sciences, Tehran, Iran

Source: Journal of Molecular Structure Published:2023

Abstract

This paper has been prepared to investigate the question why the five-membered ring formation to give Enzalutamide, needs at least a portion of dimethyl sulfoxide (DMSO) as the solvent and a high level of temperature about 95 °C?. By understanding the role of DMSO as solvent in the mechanism of such ring closing, this question might be answered. In addition, with the aid of the potential energy surface (PES) (dE) calculations, and the density functional theory (DFT) investigations, the PES curves of the reaction were designed to find the probable energy valleys and barriers of the process. The results of the experimental as well as theoretical studies showed that by choosing a suitable catalyst in DMSO: Isopropyl acetate (IPOAC) as the solvent mixture, we could handle the synthesis of Enzalutamide anti-cancer active pharmaceutical ingredient (API) in a milder condition with a lower temperature (about 70 °C), and also a shorter time (about 18 h instead of 24 h). Also, the developed HPLC-UV method showed that after crystallization, the API powder would have a total purity profile up to 99%. © 2023 Elsevier B.V.

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Experts (# of related papers)

Mohamad Amin Rezvanfar (1)

Loghman Firoozpour (1)

Style	Citing Format
MLA	Siadati SA, et al.. "The Synthesis and the Mechanism of a Five-Membered Ring Formation Between an Isothiocyanate and an Amide Leading to the Yield of Enzalutamide Anticancer Api; a Joint Experimental and Theoretical Study." Journal of Molecular Structure, vol. 1280, no. , 2023, pp. -.
APA	Siadati SA, Davoudi S, Soheilizad M, Firoozpour L, Payab M, Bagherpour S, Kolivand S (2023). The Synthesis and the Mechanism of a Five-Membered Ring Formation Between an Isothiocyanate and an Amide Leading to the Yield of Enzalutamide Anticancer Api; a Joint Experimental and Theoretical Study. Journal of Molecular Structure, 1280(), -.
Chicago	Siadati SA, Davoudi S, Soheilizad M, Firoozpour L, Payab M, Bagherpour S, Kolivand S. "The Synthesis and the Mechanism of a Five-Membered Ring Formation Between an Isothiocyanate and an Amide Leading to the Yield of Enzalutamide Anticancer Api; a Joint Experimental and Theoretical Study." Journal of Molecular Structure 1280, no. (2023): -.
Harvard	Siadati SA et al. (2023) 'The Synthesis and the Mechanism of a Five-Membered Ring Formation Between an Isothiocyanate and an Amide Leading to the Yield of Enzalutamide Anticancer Api; a Joint Experimental and Theoretical Study', Journal of Molecular Structure, 1280(), pp. -.
Vancouver	Siadati SA, Davoudi S, Soheilizad M, Firoozpour L, Payab M, Bagherpour S, et al.. The Synthesis and the Mechanism of a Five-Membered Ring Formation Between an Isothiocyanate and an Amide Leading to the Yield of Enzalutamide Anticancer Api; a Joint Experimental and Theoretical Study. Journal of Molecular Structure. 2023;1280():-.
BibTex	@article{ author = {Siadati SA and Davoudi S and Soheilizad M and Firoozpour L and Payab M and Bagherpour S and Kolivand S}, title = {The Synthesis and the Mechanism of a Five-Membered Ring Formation Between an Isothiocyanate and an Amide Leading to the Yield of Enzalutamide Anticancer Api; a Joint Experimental and Theoretical Study}, journal = {Journal of Molecular Structure}, volume = {1280}, number = {}, pages = {-}, year = {2023} }
RIS	TY - JOUR AU - Siadati SA AU - Davoudi S AU - Soheilizad M AU - Firoozpour L AU - Payab M AU - Bagherpour S AU - Kolivand S TI - The Synthesis and the Mechanism of a Five-Membered Ring Formation Between an Isothiocyanate and an Amide Leading to the Yield of Enzalutamide Anticancer Api; a Joint Experimental and Theoretical Study JO - Journal of Molecular Structure VL - 1280 IS - SP - EP - PY - 2023 ER -

Style

Citing Format

MLA

Siadati SA, et al.. "The Synthesis and the Mechanism of a Five-Membered Ring Formation Between an Isothiocyanate and an Amide Leading to the Yield of Enzalutamide Anticancer Api; a Joint Experimental and Theoretical Study." Journal of Molecular Structure, vol. 1280, no. , 2023, pp. -.

APA

Siadati SA, Davoudi S, Soheilizad M, Firoozpour L, Payab M, Bagherpour S, Kolivand S (2023). The Synthesis and the Mechanism of a Five-Membered Ring Formation Between an Isothiocyanate and an Amide Leading to the Yield of Enzalutamide Anticancer Api; a Joint Experimental and Theoretical Study. Journal of Molecular Structure, 1280(), -.

Chicago

Siadati SA, Davoudi S, Soheilizad M, Firoozpour L, Payab M, Bagherpour S, Kolivand S. "The Synthesis and the Mechanism of a Five-Membered Ring Formation Between an Isothiocyanate and an Amide Leading to the Yield of Enzalutamide Anticancer Api; a Joint Experimental and Theoretical Study." Journal of Molecular Structure 1280, no. (2023): -.

Harvard

Siadati SA et al. (2023) 'The Synthesis and the Mechanism of a Five-Membered Ring Formation Between an Isothiocyanate and an Amide Leading to the Yield of Enzalutamide Anticancer Api; a Joint Experimental and Theoretical Study', Journal of Molecular Structure, 1280(), pp. -.

Vancouver

Siadati SA, Davoudi S, Soheilizad M, Firoozpour L, Payab M, Bagherpour S, et al.. The Synthesis and the Mechanism of a Five-Membered Ring Formation Between an Isothiocyanate and an Amide Leading to the Yield of Enzalutamide Anticancer Api; a Joint Experimental and Theoretical Study. Journal of Molecular Structure. 2023;1280():-.

BibTex

@article{ author = {Siadati SA and Davoudi S and Soheilizad M and Firoozpour L and Payab M and Bagherpour S and Kolivand S}, title = {The Synthesis and the Mechanism of a Five-Membered Ring Formation Between an Isothiocyanate and an Amide Leading to the Yield of Enzalutamide Anticancer Api; a Joint Experimental and Theoretical Study}, journal = {Journal of Molecular Structure}, volume = {1280}, number = {}, pages = {-}, year = {2023} }

RIS

TY - JOUR
AU - Siadati SA
AU - Davoudi S
AU - Soheilizad M
AU - Firoozpour L
AU - Payab M
AU - Bagherpour S
AU - Kolivand S
TI - The Synthesis and the Mechanism of a Five-Membered Ring Formation Between an Isothiocyanate and an Amide Leading to the Yield of Enzalutamide Anticancer Api; a Joint Experimental and Theoretical Study
JO - Journal of Molecular Structure
VL - 1280
IS -
SP -
EP -
PY - 2023
ER -

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