Verazide

Base Information

• Chemical Name: Verazide
• CAS No.: 93-47-0
• Molecular Formula: C15H15 N3 O3
• Molecular Weight: 285.302
• Hs Code.: 2933399090
• UNII: XO8D6I4I5L
• DSSTox Substance ID: DTXSID4045002
• NCI Thesaurus Code: C81591
• ChEMBL ID: CHEMBL2104481
• Mol file: 93-47-0.mol

Synonyms:Verazide;Nicotazide;Verazina;N'-Veratrylideneisoniazid;Verazide [INN:BAN];UNII-XO8D6I4I5L;XO8D6I4I5L;Verazidum;DTXSID4045002;N'-Veratryliden-isonicotinohydrazid;N'-(3,4-dimethoxybenzylidene)isonicotinohydrazide;1-Isonicotinoyl-2-verotrylidenhydrazin;NSC 180261;NSC-180261;93-47-0;1-Isonicotinoyl-2-veratrylidenehydrazine;NCGC00160656-01;DTXCID2025002;N'-[(E)-(3,4-dimethoxyphenyl)methylidene]pyridine-4-carbohydrazide;CAS-93-47-0;SMR000718660;C15H15N3O3;Verazid;NSC180261;Isonicotinic acid, veratrylidenehydrazide;INH 3,4diMeOPhC;VERAZIDE [INN];VERAZIDE [MI];MLS001249447;MLS001249475;VERATRYLIDENE-ISONIAZID;SCHEMBL564065;CHEMBL2104481;NIOSH/NS1410000;Tox21_111963;STK072883;AKOS001569167;Tox21_111963_1;NCGC00160656-02;CS-0367735;NS14100000;3,4-dimethoxybenzylideneisonicotinoylhydrazone;3,4-Dimethoxyybenzaldehyde isonicotinoyl hydrazone;Isonicotinic acid, (3,4-dimethoxybenzylidene)hydrazide;3,4-DIMETHOXYBENZALDEHYDE ISONICOTINOYLHYDRAZONE;N'-[(E)-(3,4-dimethoxyphenyl)methylidene]isonicotinohydrazide;N-[(E)-(3,4-dimethoxyphenyl)methyleneamino]pyridine-4-carboxamide;4-PYRIDINECARBOXYLIC ACID, ((3,4-DIMETHOXYPHENYL)METHYLENE)HYDRAZIDE;4-PYRIDINECARBOXYLIC ACID, 2-((3,4-DIMETHOXYPHENYL)METHYLENE)HYDRAZIDE

Chemical Property of Verazide

Chemical Property:

• Melting Point: 189-190°
• PSA: 72.81000
• Density: 1.19g/cm³
• LogP: 2.25360
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 285.11134135
• Heavy Atom Count: 21
• Complexity: 356

Purity/Quality:

99% ^*data from raw suppliers

Verazide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C=NNC(=O)C2=CC=NC=C2)OC
• Isomeric SMILES: COC1=C(C=C(C=C1)/C=N/NC(=O)C2=CC=NC=C2)OC
• Uses: Verazide is derived from Isoniazid (I821450), which is an antibiotic for treatment of Mycobacterium tuberculosis, inhibits mycolic acid biosynthesis. Metabolized by hepatic N-acetyltransferase (NAT) and cytochrome P450 2E1 (CYP2E1) to form hepatotoxins. Selectively induces expression of CYP2E1. Reversibly inhibits CYP2C19 and CYP3A4 activities, and mechanistically inactivates CYP1A2, CYP2A6, CYP2C19 and CYP3A4 at clinically relevant concentrations. Antibacterial (tuberculostatic).

Technology Process of Verazide

There total 2 articles about Verazide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

isoniazid (54-85-3,7640-37-1) + 3,4-dimethoxy-benzaldehyde (120-14-9) → (E)-N’-(3',4'-dimethoxybenzylidene)isonicotinohydrazide (93-47-0)

Guidance literature:

With acetic acid; In ethanol; Reflux;

DOI:10.1016/j.bmc.2017.02.044

Reference yield:

isoniazid (54-85-3,7640-37-1) + 3,4-dimethoxy-benzaldehyde (120-14-9) → N-isonicotinamido-3,4-dimethoxybenzalaldimine (93-47-0)

Guidance literature:

With acetic acid; In ethanol; for 5h; Reflux;

DOI:10.4067/S0717-97072010000300019

Reference yield: 67.0%

N-isonicotinamido-3,4-dimethoxybenzalaldimine (93-47-0) + acetic anhydride (108-24-7) → 2-(3,4-dimethoxyphenyl)-3-acetyl-5-(pyridin-4-yl)-2,3-dihydro-1,3,4-oxadiazole (1314013-42-7)

Guidance literature:

Reflux;

DOI:10.1021/jm2002876

upstream raw materials:

isoniazid

3,4-dimethoxy-benzaldehyde

Downstream raw materials:

N-[5-(3',4'-dimethoxyphenyl)-1H-1,2,3-triazol-1-yl]isonicotinamide

2-(3,4-dimethoxyphenyl)-3-acetyl-5-(pyridin-4-yl)-2,3-dihydro-1,3,4-oxadiazole

Refernces

• 1、 Hayat, Muhammad,Khan, Khalid Mohammed,Saeed, Sumayya,Salar, Uzma,Khan, Momin,Baig, Taimoor,Ahmad, Aqeel,Parveen, Shahnaz,Taha, Muhammad. "Antimicrobial activities of synthetic arylidine nicotinic and isonicotinic hydrazones". . p. 1057 - 1067. Retrieved 2018/10/31.
• 2、 Malhotra, Manav,Sharma, Gaurav,Deep, Aakash. "Synthesis and characterization of (E)-N′-(substituted benzylidene)isonicotinohydrazide derivatives as potent antimicrobial and hydrogen peroxide scavenging agents". experimental part. p. 637 - 644. Retrieved 2012/08/29.