4813-04-1

Upstream product

• 54-85-3 isoniazid 
• 67-64-1 acetone 

Downstream Products

• 54-92-2 iproniazid 
• 15420-02-7 2,5-bis(4-pyridyl)-1,3,4-oxadiazole 
• 1567-89-1 N-(2,4-dinitrophenyl)-N'-isopropylidene-hydrazine 

Relevant academic research and scientific papers

Cobalt(II) compounds with acetone isonicotinoyl hydrazone tautomers: Syntheses and crystal structures of complexes with free donor atoms

Complexes with free donor atoms, as potential metalloligands, are important building blocks in crystal engineering of coordination polymers and metal organic frameworks. In this work, the possibility of formation of cobalt(II) complexes with free N-donor atoms based on acetone isonicotinoyl hydrazone (Hisn), is verified. Syntheses, X-ray crystal structures and spectroscopic properties of two new cobalt(II) compounds with this hydrazone, are reported. The structural studies reveal the formation of a cationic complex in [Co(Hisn)2(H2O)2](NO3)2 (1) containing keto ligands (Hisn) as well as a neutral complex [Co(isn)2(py)2]n (2), with the deprotonated hydrazone (isn) in its enolate form. Both complexes, with two various tautomers of the hydrazone, contain uncoordinated pyridyl groups that allows to regard them as potential N-donor metalloligands.

Thinking Outside the "blue Box": Induced Fit within a Unique Self-Assembled Polycationic Cyclophane

We present herein the development of a new polycationic molecular receptor, inspired by the ubiquitous cyclobis(paraquat-p-phenylene)cyclophane ("blue box"). Our analogue, the "white box", has been easily self-assembled on a preparative scale in water, using a template-assisted process by acyl hydrazone bonding of complementary bis(pyridinium)xylylene tweezers, followed by kinetic trapping of the empty receptor. The obtained macrocycle was found to display a marked pH responsiveness in water, because of an abnormal acidity of the amide protons within its structure. Consequently, and because of the concurrence of rotational isomerism under acidic conditions (fixed at higher pH values), the compound was found to display a dual behavior as a conformationally locked/flexible molecular host, being able to recognize appropriate aromatic substrates, in a lock and key or induced fit fashion, by a conjunction of π-π, C-H···π, and, crucially, the hydrophobic effect.

Discovery of a novel series of indolyl hydrazide derivatives as diacylglycerol acyltransferase-1 inhibitors

A novel series of hydrazide derivatives were synthesized as potential diacylglycerol acyltransferase (DGAT) inhibitors. Among them, compounds 8u and 8v exhibited selective and potent DGAT-1 inhibitory activities. In addition, compound 8u dose-dependently inhibited triglyceride synthesis in HepG2 cell lines. Furthermore, treatment with compound 8u for an oral lipid tolerance test showed a significant decrease in plasma triglyceride levels compared with vehicle-treated control animals, indicating delayed absorption of triglyceride after an acute lipid challenge.

Covalent assistance to supramolecular synthesis: Modifying the drug functionality of the antituberculosis API isoniazid in situ during co-crystallization with GRAS and API compounds

The anti-tuberculosis molecule isonicotinic acid hydrazide (isoniazid) is a promising molecule in the supramolecular synthesis of multi-component molecular complexes and also allows for its biological activity to be improved and modified by a simple covalent reaction. The low temperature crystal structures of both isoniazid (1) and the related N′-(propan-2-ylidene) isonicotinohydrazide molecule (2), the latter known to be a more effective agent against Mycobacterium tuberculosis, are reported. In addition, these two molecules were then co-crystallized with the same three Generally Regarded As Safe (GRAS) molecules, succinic acid, 4-hydroxybenzoic acid and 2-hydroxybenzoic acid, to produce the following pharmaceutical co-crystals: (isonicotinic acid hydrazide)2·(succinic acid) 3, (N′-(propan-2-ylidene) isonicotinohydrazide)2·(succinic acid) 4, (isonicotinic acid hydrazide)·(4-hydroxybenzoic acid) 6, (N′-(propan-2-ylidene) isonicotinohydrazide)·(4-hydroxybenzoic acid) 7, (isonicotinic acid hydrazide)·(2-hydroxybenzoic acid) 8, and (N′-(propan-2-ylidene) isonicotinohydrazide)·(2-hydroxybenzoic acid) 9. In addition, a co-crystal using 2-butanone as a modifier is also reported, (N′-(butan-2- ylidene)isonicotinohydrazide)2·(succinic acid) 5. Drug-drug co-crystals were also made with the anti-HIV compound 2-chloro-4-nitrobenzoic acid: (isonicotinic acid hydrazide)·(2-chloro-4-nitrobenzoic acid) 10, and (N′-(propan-2-ylidene)isonicotinohydrazide)·(2-chloro-4- nitrobenzoic acid) 11. All the co-crystals use the carboxylic acid...pyridine hydrogen bond to connect the GRAS or drug molecule to the pyridine ring. In general, the co-crystals with the modified isoniazid feature the C(4) homosynthon, and those with the original isoniazid a variety of homo- and heterosynthons. By comparing the melting points of the co-crystals that use isoniazid and those that use the modified isoniazid, a reduction in melting point is observed. The Royal Society of Chemistry 2012.

Preparation and antitubercular activities in vitro and in vivo of novel Schiff bases of isoniazid

Structural modification of the frontline antitubercular isonicotinic acid hydrazide (INH) provides lipophilic adaptations (3-46) of the drug in which the hydrazine moiety of the parent compound has been chemically blocked from the deactivating process of N2-acetylation by N-arylaminoacetyl transferases. As a class, these compounds show high levels of activity against Mycobacterium tuberculosis in vitro and in tuberculosis-infected macrophages. They provide strong protection in tuberculosis-infected mice and have low toxicity. With some representatives of this class achieving early peak plasma concentrations approximately three orders of magnitude above minimum inhibitory concentration, they may serve as tools for improving our understanding of INH-based treatment modalities, particularly for those patients chronically underdosed in conventional INH therapy.

Dioxouranium(VI) Complexes of Acetone Isonicotinylhydrazone

New complexes of acetone isonicotinoylhydrazone (IH) with uranyl nitrate, acetate and thiocyanate of the types UO2 (AIH)X2 and UO2(AIH)2X2 have been isolated and characterized by analytical, melting point, molar conductance and infrared and Raman spectral data.It is shown that in UO2(AIH)X2 complexes, the ligand molecule, although a potentially tetradentate ligand, acts in a neutral tridentate manner and coordinates to one uranium atom through carbonyl oxygen and azomethine nitrogen atom and to another uranium atom through puridine nitrogen atom in a bridging manner.In UO2(AIH)2X2 complexes, one ligand molecule acts as a tridentate bridging ligand and the other ligand molecule acts as a monodentate ligand bonding terminally through pyridine ring nitrogen atom only to the uranyl group.Nitrato, acetato and thiocyanato groups act as terminal monodentate ligands.

Triorganotin(IV) Complexes of Isonicotinoyl Hydrazones

Five-coordinated triorganotin(IV) complexes of isonicotinoyl hydrazones (LH) of various aldehydes or ketones with the formula R3SnL (where R=Bu, Ph, or Bz and L=anion of the hydrazone) have been synthesised.The complexes are monomeric in benzene and non-electrolytes in methanol; they have been assigned trigonal-bipyramidal geometry.