Solid-phase synthesis of substituted guanidines using a novel acid labile linker

Journal of Combinatorial Chemistry

Volumn 2, Issue 4, 2000, Pages 370-377

  Pátek, Marcel ^a   Smrčina, Martin ^a   Nakanishi, Eiji ^b   Izawa, Hiroyuki ^b  

^a Selectide Corporation   (United States)

^b AJINOMOTO CO INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; GUANIDINE DERIVATIVE; PYRAZOLE DERIVATIVE; TRIFLUOROACETIC ACID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DESIGN; PH; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMINES; DRUG DESIGN; GUANIDINES; HYDROGEN-ION CONCENTRATION; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRAZOLES; STRUCTURE-ACTIVITY RELATIONSHIP; TRIFLUOROACETIC ACID;

EID: 0034223083     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc0000141     Document Type: Article

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23. 1,2- and 1,3-diamines provided corresponding cyclic guanidines.
24. 3CN) with the following isolated yields: 8b (68%), 8f (65%), 81 (83%).
25. Process of building blocks selection was as follows: building blocks for R1, R2, and R3 were obtained from Available Chemicals Database (ACD). Large data sets of structures were first filtered applying internal criteria such as unwanted fragments, reactive groups, MW cutoff, and library size. In the next step, a virtual library of substituted guanidines was enumerated with the filtered R-groups. Further selection of building blocks was done using 2D fingerprints and Tanimoto index (cutoff at 0.85) as implemented in Diversity Manager software (Tripos). At this stage, 29 alcohols and 22 anilines were identified for chemistry evaluation in plates. The final list of building blocks for each position (10 + 8 alcohols and 11 anilines) was "fine-tuned" to reflect chemistry performance (purity criteria).