Abstract

A series of estrone derivatives, 2–4, were synthesized from the corresponding arylidine estrone, 2a,b, as starting materials, which were prepared by condensation of estrone (3-hydroxy-estran-17-one, 1) with 4-bromobenzaldehyde and thiophene-2-aldehyde. Treating of 2a,b with hydrazine derivatives in acetic acid or propionic acid afforded pyrazoline derivatives, 3a–f and 4a–f, respectively. Furthermore, results proved the superiority of thienyl derivatives over 4-bromophenol derivatives in terms of cytotoxic effects on MCF-7 cancer cells. In vivo xenograft breast cancer animal model experiments revealed that the synthesized derivatives can be used for decreasing tumor volume, while the most potent derivative (4f) decreased the development of tumor volume by about 87.0% after 12 days.

Highlights

  • Estrone (Figure 1) is a steroid, a weak weak estrogen, estrogen, a minor minor female female sex hormone [1], is synthesized from androstadienedione, and secreted mainly from the gonads, though it can be formed from adrenal androgens androgens in in adipose adipose tissue tissue [2]. [2]

  • Treating of arylidene derivatives 2a,b with hydrazine hydrate, methyl hydrazine, or phenyl hydrazine hydrazine in glacial acetic acid afforded the corresponding pyrazoline derivatives, 3a–f, confined to in glacial acetic acid afforded the corresponding pyrazoline derivatives, 3a–f, confined to ring D of ring D of the steroidal scaffold with acetylation of the 3-phenolic hydroxyl

  • Treating of arylidene the steroidal scaffold with acetylation of the 3-phenolic hydroxyl

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Summary

Introduction

Estrone (Figure 1) is a steroid, a weak weak estrogen, estrogen, a minor minor female female sex hormone [1], is synthesized from androstadienedione, and secreted mainly from the gonads, though it can be formed from adrenal androgens androgens in in adipose adipose tissue tissue [2]. [2]. Estrone (Figure 1) is a steroid, a weak weak estrogen, estrogen, a minor minor female female sex hormone [1], is synthesized from androstadienedione, and secreted mainly from the gonads, though it can be formed from adrenal androgens androgens in in adipose adipose tissue tissue [2].

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