2,3-Diaryl-2,3-Dihydro-1,3-Thiazin-4-Ones for Broad Bioactivity

Resolve Bottlenecks,
Find Innovative SolutionsGenerate Solutions

Solution Overview

Problem

Existing compounds with 1,3-thiazin-4-one scaffolds have shown limited bioactivity profiles, particularly in areas such as antifungal, antitubercular, antitumor, antimalarial, and HIV-RT inhibitory activities, necessitating the development of novel compounds with enhanced biological properties.

Innovation Solution

The synthesis of 2,3-diaryl-2,3-dihydro-4H-1,3-thiazin-4-ones, where R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, and R14 are independently selected from specific groups including H, halogen, nitro, cyano, amido, pyridyl, alkyl, aryl, acyl, alkoxy, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, and heteroaryl, to create compounds with diverse structural variations.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If existing 1,3-thiazin-4-one scaffold compounds are used, then the basic structure is simple, but the bioactivity profile is limited

Engineering Contradiction:

Improvebioactivity profileVSAvoidstructural complexity

Core Design Contradiction:

Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The molecule is divided into distinct functional segments: the core 1,3-thiazin-4-one scaffold (R3-R8) and multiple aryl substituents (R1-R2, R9-R14) that can independently contribute different bioactivities. This segmentation allows each region to be optimized for specific functions while maintaining overall molecular integrity

Inventive Principle:

Principle #1Segmentation

Solution Approach 2:

The patent creates composite molecular structures by combining the 1,3-thiazin-4-one core with diverse aryl groups (phenyl, naphthyl, heteroaryl) and substituent patterns. This composite approach integrates multiple functional characteristics into a single molecule, expanding bioactivity profiles beyond what the simple scaffold alone could achieve

Inventive Principle:

Principle #40Composite materials

2Reliability

If diverse substituents are introduced to enhance bioactivity, then the biological efficacy improves, but the synthesis complexity increases

Engineering Contradiction:

Improvebiological efficacyVSAvoidsynthesis complexity

Core Design Contradiction:

ReliabilityVSEase of manufacture

Solution Approach 1:

The core 1,3-thiazin-4-one scaffold serves as a universal platform that can accommodate multiple different substituent patterns (R1-R14) while maintaining the fundamental bioactive core. This multi-functionality allows a single synthesis route to potentially generate multiple bioactive variants with different aryl substitutions

Inventive Principle:

Principle #6Universality (Multi-functionality)

Solution Approach 2:

The patent systematically varies substituent parameters (aryl group types, positions, and combinations) around the fixed core scaffold. By changing these molecular parameters while maintaining the core structure, the invention optimizes biological efficacy through combinatorial chemistry approaches without requiring complete redesign of the synthesis pathway

Inventive Principle:

Principle #35Parameter changes

Data Source

PatentUS20250326727A12,3-diaryl-2,3-dihydro-4h-1,3-thiazin-4-one compounds and methods for making

Publication Date: 2025.10.23 THE PENN STATE RES FOUND INC

AI summary

A compound with the following general formula and a general method of making this compound are provided:R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13 and R14 are each independently selected from the group that includes H, halogen, nitro, cyano, amido, pyridyl, alkyl, aryl, acyl, alkoxy, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, heteroaryl and heteroaralkyl.