1,2-Dihydroquinoline Derivatives with Phenylchalcogeno and Ester Groups
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Solution Overview
Problem
Current compounds with a 1,2-dihydroquinoline structure do not specifically incorporate substituted phenylchalcogeno lower alkyl groups and ester-introduced phenyl groups, limiting their potential as glucocorticoid receptor modulators for various diseases.
Innovation Solution
Development of novel 1,2-dihydroquinoline derivatives with substituted phenylchalcogeno lower alkyl groups and ester-introduced phenyl groups, which exhibit glucocorticoid receptor binding activity, serving as modulators for diseases related to metabolic, inflammatory, autoimmune, and central nervous system disorders.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If conventional 1,2-dihydroquinoline structures are used, then the basic framework is simple and well-established, but they lack specific substituted phenylchalcogeno lower alkyl groups and ester-introduced phenyl groups, limiting glucocorticoid receptor modulator activity
Solution Approach 1:
The patent applies local quality by introducing specific functional groups (substituted phenylchalcogeno lower alkyl groups at position 5 and ester-introduced phenyl groups at position 6) into specific locations of the 1,2-dihydroquinoline core structure. This localized modification enhances glucocorticoid receptor binding activity while maintaining the overall molecular framework, resolving the contradiction between structural simplicity and biological activity.
Solution Approach 2:
The patent creates a composite molecular structure by combining the 1,2-dihydroquinoline core with multiple distinct functional groups (phenylchalcogeno lower alkyl groups containing O, S, or Se atoms, and ester-introduced phenyl groups). This composite approach integrates different chemical functionalities into a single molecule, achieving enhanced receptor binding activity through the synergistic effect of multiple structural elements.
2Reliability
If novel substituted groups are introduced to enhance receptor binding activity, then pharmacological effectiveness improves, but synthesis complexity and manufacturing difficulty increase
Solution Approach 1:
The patent employs segmentation by dividing the molecule into distinct functional segments: the 1,2-dihydroquinoline core, the phenylchalcogeno lower alkyl group at position 5, and the ester-introduced phenyl group at position 6. Each segment can be independently synthesized and characterized, allowing for modular optimization of pharmacological activity while facilitating systematic synthesis planning and manufacturing scalability.
Data Source
AI summary
To study the synthesis of novel 1,2-dihydroquinoline derivative having substituted phenylchalcogeno lower alkyl group and ester-introduced phenyl group as substituents and a salt thereof, and to find a pharmacological action of the derivative and a salt thereof. The compounds represented in general formula (1) and a salt thereof are useful for glucocorticoid receptor modulator. The R1 represents a hydrogen atom or a lower alkyl group; R2 represents a hydrogen atom or a lower alkyl group; R3 and R4 may be the same or different and represent a hydrogen atom or a lower alkyl group; R5 represents a hydrogen atom or a lower alkyl group; R6 represents a halogen atom, a lower alkyl group, a hydroxy group, a lower alkoxy gorup or a nitro group; X represents -C(O)-, -C(O)NR8-, -S(O)2- and the like; R7 and/or R8 may be the same or different and represent a hydrogen atom, a lower alkyl group which may have a substituent, an aryl group which may have a substituent, a heterocyclic group which may have a substituent, a lower alkoxy group which may have a substituent and the like; Y represents a lower alkylene group; Z represents a chalcogen atom; and P represents 0, 1, 2 or 3.