Nicotinohydrazide (nicotinic acid hydrazide) is an antimicrobial and antitubercular drug. It acts by binding to nicotinamidase, converting to an active metabolite, and then interfering with bacterial metabolism, disrupting its growth and proliferation." />

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Chemical Structure| 553-53-7 Chemical Structure| 553-53-7
Chemical Structure| 553-53-7

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CAS No.: 553-53-7

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Nicotinohydrazide (nicotinic acid hydrazide) is an antimicrobial and antitubercular drug. It acts by binding to nicotinamidase, converting to an active metabolite, and then interfering with bacterial metabolism, disrupting its growth and proliferation.

Synonyms: Nicotinic acid hydrazide

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Hegde, Pooja Venkatesh ;

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......................

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Hegde, Pooja ; Boshoff, Helena I. M. ; Rusman, Yudi ; Aragaw, Wassihun Wedajo ; Salomon, Christine E. ; Dick, Thomas , 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

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Alternative Products

Product Details of Nicotinohydrazide

CAS No. :553-53-7
Formula : C6H7N3O
M.W : 137.14
SMILES Code : NNC(C1=CC=CN=C1)=O
Synonyms :
Nicotinic acid hydrazide
MDL No. :MFCD00006383
InChI Key :KFUSANSHCADHNJ-UHFFFAOYSA-N
Pubchem ID :11112

Safety of Nicotinohydrazide

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Nicotinohydrazide

* 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.

  • Downstream synthetic route of [ 553-53-7 ]

[ 553-53-7 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 6938-06-3 ]
  • [ 553-53-7 ]
YieldReaction ConditionsOperation in experiment
78.7% With hydrazine hydrate; In ethanol; for 6.0h;Reflux; General procedure: The obtained compounds II was dissolved with ethanol (90 mL) and hydrazine hydrate (85percent, 30 mL),then the mixture was heated to reflux for 6 h. After the reaction was completed, ethanol and the excess of hydrazine hydrate were distilled out under a reduced pressure, and a white product was left. The crude product was recrystallized from ethanol to afford white crystals III.
  • 2
  • [ 553-53-7 ]
  • [ 103854-64-4 ]
  • C17H14N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 80℃; for 3h; General procedure: 8-Methoxyquinoline-2-carbaldehyde (25, 0.534 mmol) was refluxedwith various substituted acylhydrazines (0.587 mmol, 1.1 eq) in ethanol(5-10 mL) to get acyl hydrazides of 8-hydroxyquinoline. After completionof reaction, quinoline acyl hydrazides were found as precipitateson cooling to -15 C. Precipitates were washed with coldethanol and dried under vacuum. These acyl hydrazides were used directlyfor one pot synthesis of 2,5-disubstituted-1,3,4-oxadiazole usingiodine/K2CO3 catalysed oxidative cyclization. To the acyl hydrazides(1.0 eq) in DMSO (5-10 mL), K2CO3 (3.0 eq) and iodine (1.2 eq) wereadded in sequence and refluxed at 110 C. After the completion, thereaction mixture was cooled and saturated solution of sodium thiosulfatewas added. The precipitates were collected and dried under highvacuum to get the respective compounds (33-50).
  • 3
  • [ 553-53-7 ]
  • [ 42926-52-3 ]
  • N'-(2′-ethoxybenzoyl)nicotinohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With pyridine; for 36h;Reflux; General procedure: N-benzoyl/nicotinoyl aryl benzohydrazides were obtained by treating different hydrazides with various derivatives of benzoyl chlorides in pyridine and the reaction mixture was refluxed for 36 h.The progress of reaction was monitored by TLC, after completion, the reaction mixture was poured onto 19% HCl, precipitates formed were filtered further washed with hot water and hexane. The solid product was crystallized from ethanol. The compounds thus obtained were characterized via EI-MS and H1-NMR. Among all synthetic derivatives,compounds 19, 37, and 40 are new while rest of the compounds are reported in the literature [25-37]
  • 4
  • [ 553-53-7 ]
  • [ 4771-48-6 ]
  • (E)-N'-((4-methyl-1H-indol-3-yl)methylene)nicotinohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With acetic acid; In ethanol; at 70℃; for 6h; The hot (70 C) ethanolic solution (20 mL) of nicotinohydrazide(0.28 g, 2.04 mmol) was added to a hot (70 C) ethanolic solution(20 mL) of 4-methyl-1H-indol-3-carbaldyhde (0.3 g, 1.89 mmol),which was initially acidified with few drops of glacial acetic acidand then reflux for 6 h. After cooling the solution, pour it in bath iceand leave it till the precipitate is formed. The formed precipitatewas filtered off, washed several times with methanol and dried in a vacuum desiccator over P4O10 (Scheme 1).
 

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