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                            Chemical Structure| 55-22-1
                            
                            Chemical Structure| 55-22-1
                        
    
    					
    
    						
    					
    
    				
    
    				
    
    					
    
    					
    
    					
    
    						
    
                                Chemical Structure| 55-22-1
                            
    
    						
    
                                
                            
    
    					
    
    				
    
                    
                    
                    
    			
    
                
    
                    
                
    
                
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    CAS No.: 55-22-1
    
                
                
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                    Isonicotinic acid is a metabolite of isoniazid. It is an isomer of nicotinic acid.
                    
                
    
    			
                
    
        			
    
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                                    Anushree Mondal
                                    
                                    
                                    ; 
                                    
                                
                                    
                                     Pronay Roy
                                    
                                    
                                    ; 
                                    
                                
                                    
                                     Jaclyn Carrannatto
                                    
                                    
                                
                                    
                                    
                                
                                    
                                    
                                
                                    
                                    
                                
                                
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    Abstract: The prenylated-flavin mononucleotide-dependent decarboxylases (also known as UbiD-like enzymes) are the most recently discovered family of decarboxylases. The modified flavin facilitates the decarboxylation of unsaturated carboxylic acids through a novel mechanism involving 1,3-dipolar cyclo-addition chemistry. UbiD-like enzymes have attracted considerable interest for biocatalysis applications due to their ability to catalyse (de)carboxylation reactions on a broad range of aromatic substrates at otherwise unreactive carbon centres. There are now ～35[thin space (1/6-em)]000 protein sequences annotated as hypothetical UbiD-like enzymes. Sequence similarity network analyses of the UbiD protein family suggests that there are likely dozens of distinct decarboxylase enzymes represented within this family. Furthermore, many of the enzymes so far characterized can decarboxylate a broad range of substrates. Here we describe a strategy to identify potential substrates of UbiD-like enzymes based on detecting enzyme-catalysed solvent deuterium exchange into potential substrates. Using ferulic acid decarboxylase (FDC) as a model system, we tested a diverse range of aromatic and heterocyclic molecules for their ability to undergo enzyme-catalysed H/D exchange in deuterated buffer. We found that FDC catalyses H/D exchange, albeit at generally very low levels, into a wide range of small, aromatic molecules that have little resemblance to its physiological substrate. In contrast, the sub-set of aromatic carboxylic acids that are substrates for FDC-catalysed decarboxylation is much smaller. We discuss the implications of these findings for screening uncharacterized UbiD-like enzymes for novel (de)carboxylase activity.
    
                                
    
                            
    
                            
                            
                            
                                
                            
                        
    
                        
                        
    
                            
                            
                        
    
                        
                        
    
                    
    
                    
                    
    
                        
    
                            
                            
                                
                            
                            
    
                            
    
                                
                                
                                    
                                    Kim, Ho Young
                                    
                                    
                                    ; 
                                    
                                
                                    
                                     Lee, Ji Youn
                                    
                                    
                                    ; 
                                    
                                
                                    
                                     Hsieh, Chia-Ju
                                    
                                    
                                
                                    
                                    
                                
                                    
                                    
                                
                                    
                                    
                                
                                
                                    , et al.
                                
                                
                                
                                    
                                
                            
    
                            
                            
    
                                
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    Abstract: Previous studies have confirmed that the binding of D3?receptor antagonists is competitively inhibited by endogenous dopamine despite excellent binding affinity for D3?receptors. This result urges the development of an alternative scaffold that is capable of competing with dopamine for binding to the D3?receptor. Herein, an SAR study was conducted on metoclopramide that incorporated a flexible scaffold for interaction with the secondary binding site of the D3?receptor. The alteration of benzamide substituents and secondary binding fragments with aryl carboxamides resulted in excellent D3?receptor affinities (Ki = 0.8–13.2 nM) with subtype selectivity to the D2?receptor ranging from 22- to 180-fold. The β-arrestin recruitment assay revealed that?21c?with 4-(pyridine-4-yl)benzamide can compete well against dopamine with the highest potency (IC50?= 1.3 nM). Computational studies demonstrated that the high potency of?21c?and its analogs was the result of interactions with the secondary binding site of the D3?receptor. These compounds also displayed minimal effects for other GPCRs except moderate affinity for 5-HT3?receptors and TSPO. The results of this study revealed that a new class of selective D3?receptor antagonists should be useful in behavioral pharmacology studies and as lead compounds for PET radiotracer development.
    
                                
    
                            
    
                            
                            
                            
    
                                
    Keywords: 
                                    D3 receptor antagonists ; metoclopramide ; bitopic ligand ; β-arrestin recruitment assay ; computational chemistry 
                                
    
                                
    
                            
    
                            
                            
                                
                            
                        
    
                        
                        
    
                            
                                
    
                            
                            
                        
    
                        
                        
    
                    
    
                    
                    
    
                        
    
                            
                            
                                
                            
                            
    
                            
    
                                
                                
                                    
                                    Hegde, Pooja Venkatesh
                                    
                                    
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    Abstract: Tuberculosis (TB) remains a leading cause of infectious disease mortality and morbidity resulting in nearly 1.3 million deaths annually and infecting nearly one-quarter of the population. Chapter 1 discusses the epidemiology, control, and management of TB. Isoniazid (INH) is a cornerstone for the treatment of drug-susceptible TB, yet the quantitative structure-activity relationships for INH are not well documented in the literature. Chapter 2 evaluates a systematic series of INH analogs against contemporary Mycobacterium tuberculosis (Mtb) strains from different lineages and several key species of non-tuberculous mycobacteria (NTM). To assess the specific activity of this series of INH analogs against mycobacteria, we assayed them against a panel of Gram-positive and Gram-negative bacteria, as well as a number of fungi. Our findings provide an updated analysis of the structure-activity relationship of INH that will serve as a valuable resource for the development of a next generation antitubercular compounds. para-Aminosalicylic acid (PAS), is an important second-line agent for treating drug-resistant Mtb. PAS has a moderate bioavailability and rapid clearance that necessitate high doses in order to facilitate an effective treatment. Consequently, such high doses commonly results in gastrointestinal disturbances (presumably by disruption of gut microbiota and host epithelial cells). Chapter 3 discusses the design, synthesis and evaluation of PAS prodrugs and analogs with improved oral bioavailability, thereby preventing intestinal accumulation as well as undesirable bioactivation by the gut microbiome to cytotoxic folate species. The pivoxyl prodrug and fluorination at the 5- position address the primary limitations of PAS and have the potential to revitalize this second-line TB drug. vi Pyrazinamide (PZA) is a critical component of the first-line TB treatment regimen because of its sterilizing activity against non-replicating Mtb, but its mechanism of action has remained enigmatic. PZA is a prodrug converted to the active moiety- pyrazinoic acid (POA), by pyrazinamidase, an amidase within the nicotinamide adenine dinucleotide (NAD) salvage pathway encoded by pncA in Mtb. PZA resistance is most commonly induced via loss-of-function mutations within PncA. It has recently been demonstrated that POA induces targeted protein degradation of the enzyme PanD, a crucial component of the coenzyme A biosynthetic pathway, essential in Mtb. Chapter 4 describes the structure activity relationship (SAR) evaluation of various POA analogs. Further development and mechanistic analysis of these analogs may lead to a next generation POA analog for treating TB. The salicylic acid derived small molecule siderophores known as mycobactins are essential for mycobacterial iron acquisition and mycobactin biosynthesis has been biochemically and genetically validated as essential for survival in vivo. Sal-AMS, a modified nucleoside derivative that mimics an intermediate in the mycobactin biosynthetic pathway, is a potent Mtb inhibitor. Chapter 5 explores polyfluorinated salicylic acid derivatives as antimetabolites, designed to antagonize mycobactin synthesis. Enzymatic studies demonstrated that the tri- and tetra- fluorinated salicylic acid analogs were neither substrates nor inhibitors of MbtA, but the di-fluorinated compounds were readily activated by the bifunctional adenylating enzyme MbtA, responsible for processing salicylic acid moieties for synthesis of mycobactins. However further microbiological analysis revealed that the polyfluorinated derivatives have low potential as anti-TB agents and do not appear to operate by inhibiting mycobactin synthesis. vii Lastly, the chemical synthesis of nucleoside analogs, an important class of compounds with applications as anti-infective, anti-cancer, and diagnostic agents, is extremely challenging, typically requiring linear synthesis, multiple protectiondeprotection sequences, and stereoselective formation of the critical glycosidic linkage. Nucleoside phosphorylases (NPs) have tremendous biocatalytic potential and aid in the selective modification of nucleosides under green conditions. Chapter 6 focuses on the functional characterization of 15 thermostable purine NPs. Four of these were further selected for a comprehensive analysis of their substrate scope. Next, chemoenzymatic methods for the synthesis of modified nucleosides were extensively studied using various coupled systems, and 12 modified nucleosides were synthesized, isolated, and characterized. viii Table of Contents Acknowledgments......................
    
                                
    
                            
    
                            
                            
                            
                                
    
                                    
    Purchased from AmBeed: 
                                         ;  ;  ;  ;  ;  ;  
                                    
    
                                    
    
                                
    
                            
                        
    
                        
                        
    
                    
    
                    
                    
    
                        
    
                            
                            
                                
                            
                            
    
                            
    
                                
                                
                                    
                                    Hegde, Pooja
                                    
                                    
                                    ; 
                                    
                                
                                    
                                     Boshoff, Helena I. M.
                                    
                                    
                                    ; 
                                    
                                
                                    
                                     Rusman, Yudi
                                    
                                    
                                
                                    
                                    
                                
                                    
                                    
                                
                                    
                                    
                                
                                    
                                    
                                
                                
                                    , et al.
                                
                                
                                
                                    
                                
                            
    
                            
                            
                            
                            
                            
    
                                
    Abstract: Isoniazid (INH) remains a cornerstone for treatment of drug susceptible tuberculosis (TB), yet the quant. structure-activity relationships for INH are not well documented in the literature. In this paper, we have evaluated a systematic series of INH analogs against contemporary Mycobacterium tuberculosis strains from different lineages and a few non-tuberculous mycobacteria (NTM). Deletion of the pyridyl nitrogen atom, isomerization of the pyridine nitrogen to other positions, replacement of the pyridine ring with isosteric heterocycles, and modification of the hydrazide moiety of INH abolishes antitubercular activity. Similarly, substitution of the pyridine ring at the 3-position is not tolerated while substitution at the 2-position is permitted with 2-methyl-INH 9 displaying antimycobacterial activity comparable to INH. To assess the specific activity of this series of INH analogs against mycobacteria, we assayed them against a panel of gram-pos. and gram-neg. bacteria, as well as a few fungi. As expected INH and its analogs display a narrow spectrum of activity and are inactive against all non-mycobacterial strains evaluated, except for 4, which has modest inhibitory activity against Cryptococcus neoformans. Our findings provide an updated anal. of the structure-activity relationship of INH that we hope will serve as useful resource for the community.
    
                                
    
                            
    
                            
                            
                            
    
                                
    Keywords: 
                                    Isoniazid ; SAR 
                                
    
                                
    
                            
    
                            
                            
                                
    
                                    
    Purchased from AmBeed: 
                                         ;  ;  ;  ; 54-92-2 ;  ;  ;  
                                    
    
                                    
    
                                
    
                            
                        
    
                        
                        
    
                    
    
                    
                
    
                
                

        		
        		
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    Product Details of [ 55-22-1 ]
     
        			
    
        				
        				
                            
        					
    CAS No. :55-22-1
    
                            
                            
        					
    Formula :
                                
                                    C6H5NO2
                                
                            
    
                            
                            
        					
    M.W : 
                                
                                    123.11  
                                
                            
    
                            
                            
        					
    SMILES Code : 
                                OC(=O)C1=CC=NC=C1
                            
    
                            
                            
                            
        					
    MDL No. :MFCD00006429
    
                            
                            
                            
        					
    InChI Key :TWBYWOBDOCUKOW-UHFFFAOYSA-N
    
                            
                            
        					
    Pubchem ID :5922
    
                            
                            
        			
    
        			
        			
        			
    Safety of [ 55-22-1 ]
    
        			
    
        				
        				
        					
                            
    GHS Pictogram:
                                
                                
                                    
                                
                                
                            
    
                            
                            
        					
    Signal Word:Warning
    
                            
                            
        					
    Hazard Statements:H315-H319-H335
    
                            
                            
                            
    Precautionary Statements:P261-P305+P351+P338
    
        					
                            
                            
                            
        				    
        			
    
        			
                    

        			
                    

        			
                    
        			
                    
        			
                    
        			
                    
        			
        			
                    
                    
    
                        
    Application In Synthesis [ 55-22-1 ]
    
                        
    * All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
    
                        
      
                            
                                
    • Upstream synthesis route of [ 55-22-1 ]
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    • Downstream synthetic route of [ 55-22-1 ]
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    [ 55-22-1 ] Synthesis Path-Upstream   1~3
    
                            
                            
                                
    
                                    
                                    
                                        
      
                                            
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    • [ 1690-75-1 ]
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                                            References:
                                            
                                                [1] Archiwum Chemji i Farmacji, 1936, vol. 3, p. 109,113[2] Chemisches Zentralblatt, 1937, vol. 108, # II, p. 74.
    
                                            
                                        
    
                                    
                                
    
                            
                                
    
                                    
                                    
                                        
      
                                            
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    • [ 75-65-0 ]
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    • [ 81660-73-3 ]
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                                            References:
                                            
                                                [1] Chemistry - A European Journal, 2015, vol. 21, # 40, p. 14030 - 14035.
    
                                            
                                                [2] Journal of the American Chemical Society, 2015, vol. 137, # 45, p. 14465 - 14472.
    
                                            
                                                [3] Journal of Chemical Research, Miniprint, 1987, # 3, p. 642 - 679.
    
                                            
                                        
    
                                    
                                
    
                            
                                
    
                                    
                                    
                                        
      
                                            
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    • [ 80194-83-8 ]
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                                            References:
                                            
                                                [1] Tetrahedron, 1989, vol. 45, # 23, p. 7469 - 7476.
    
                                            
                                        
    
                                    
                                
    
                            
                        
    
                        
                        
                        
                    
    
                    

        			
     
    
        		
    
        		
                
                
        		
                
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