US 12358943 B1Patent grantUnited States

Steroid-Linked Compounds for Antimicrobial Screening

Official patent title

Method of synthesizing testosterone-based thiazolidinone derivatives

Arabic title: طريقة لتخليق مشتقات الثيازوليدينون القائمة على التستوستيرون

Invention

Problem

Antimicrobial resistance creates demand for new chemical scaffolds, while synthesizing steroid-linked thiazolidinones with reproducible structures and measurable microbial activity requires controlled multistep chemistry.

Why it matters

New antimicrobial candidates may expand early discovery options against bacteria and fungi, but activity in laboratory cultures does not by itself demonstrate safety or therapeutic efficacy.

Approach

The method converts testosterone to a thiosemicarbazone intermediate and then cyclizes it with an acetylenedicarboxylate or an N-aryl maleimide. The resulting testosterone-based thiazolidinone derivatives are structurally characterized and described as producing inhibition zones against selected bacterial and fungal strains.

Who may benefit

Potential beneficiaries include medicinal-chemistry groups, antimicrobial discovery laboratories, pharmaceutical researchers, university chemistry programs, and contract research teams conducting early microbial screening.

Potential value

The disclosure offers a defined steroid-to-thiazolidinone synthesis platform with several cyclization partners and initial in-vitro antimicrobial screening endpoints.

Background

Antimicrobial resistance has reduced the effectiveness of established drugs and increased interest in new molecular classes. Thiazolidinones are studied because substitution around the ring can alter biological activity, while steroid conjugation offers another route to chemical diversity. The publication prepares testosterone-linked derivatives through a thiosemicarbazone intermediate and reports agar inhibition-zone thresholds against two bacteria and two fungi. These are early in-vitro observations; the supplied record does not establish minimum inhibitory concentrations, selectivity, mammalian toxicity, pharmacology, animal efficacy, or clinical benefit.

Technology overview

Thiosemicarbazide and testosterone solutions are reacted in an acidic medium at about 60–80 °C for six to eight hours to form testosterone thiosemicarbazone. This intermediate is isolated and cyclized in an organic solvent with DMAD or related acetylenedicarboxylates, or with N-phenyl, N-(4-chlorophenyl), or N-benzyl maleimide. Reaction schemes and proton NMR spectra support synthesis and structure assignment. The disclosure states inhibition-zone diameters against Staphylococcus aureus, Escherichia coli, Candida albicans, and Aspergillus niger.

Potential applications

Early-stage antimicrobial compound screening.
Medicinal-chemistry libraries of steroid-linked thiazolidinones.
Research probes for bacterial and fungal growth assays.
Structure-activity studies using alternative cyclization partners.

Evidence-supported advantages

The route uses a common testosterone thiosemicarbazone intermediate.
Several acetylenedicarboxylate and N-aryl maleimide variants are contemplated.
Reaction conditions and solvent alternatives are specified.
Proton NMR characterization and microbial inhibition-zone endpoints are described.

Development stage

Laboratory synthesis, proton-NMR characterization, and in-vitro inhibition-zone screening are described; cytotoxicity, in-vivo efficacy, and clinical validation are not established.

Commercial opportunity

The chemistry could support an antimicrobial lead-discovery program or compound-library licensing. Advancement requires independent MIC and kill-kinetic studies, resistant clinical isolates, selectivity and cytotoxicity testing, mechanism work, formulation, pharmacokinetics, animal efficacy, manufacturing controls, and regulatory development. No human therapeutic efficacy or safety is established.

Patent classifications

WIPO IPC

C07J43/00Steroids
A01N45/00Preservation of human, animal or plant bodies or parts thereof; biocides, pesticides and herbicides; pest repellants or attractants; plant growth regulators

CPC

A01N45/00Preservation of human, animal or plant bodies or parts thereof; biocides, pesticides and herbicides; pest repellants or attractants; plant growth regulators
A01P1/00Biocidal, pest-repellent, pest-attractant or plant-growth-regulatory activity of chemical compounds or preparations
A01P3/00Biocidal, pest-repellent, pest-attractant or plant-growth-regulatory activity of chemical compounds or preparations
C07J43/003Steroids

Inventors

First inventorMortaga Mohamed M. Abou-Krisha
InventorAbdulrahman G. ALHAMZANI
InventorAl-Hassan S. Mahdy
InventorEhab Abdelhamed Abdelrahman Ahmed
InventorMohamed Abd-Elsabour
InventorAbdullah A. Aldakhil

Keywords

testosterone
thiazolidinone
thiosemicarbazone
cyclization
antimicrobial
inhibition zone
N-aryl maleimide
medicinal chemistry

Patent document and drawings

The patent publication is mapped to this record. Patent drawings remain within that publication; no separately cleared public media package has been supplied.