The hierarchies of hydrogen bonds in salts/cocrystals of isoniazid and its Schiff base – a case study

Oruganti, Madhavi; Khade, Pavan A.; Das, Uttam Kumar; Trivedi, Darshak R.

doi:10.1039/c5ra14951g

Cited by 18 publications

(11 citation statements)

References 49 publications

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“…Lemmerer et al synthesized various isoniazid derivatives by using different ketone modifiers and designed the corresponding cocrystals [27]. Oruganti et al designed different cocrystals using isoniazid and N -(propan-2-ylidene)-isonicotinohydrazide, a derivative of isoniazid [28]. In this study, N -(propan-2-ylidene)-isonicotinohydrazide, an isoniazid derivative, was synthesized and isolated through sonocrystallization.…”

Section: Introductionmentioning

confidence: 99%

Sonocrystallization—Case Studies of Salicylamide Particle Size Reduction and Isoniazid Derivative Synthesis and Crystallization

Yang

Yen

et al. 2018

Crystals

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Two case studies of salicylamide particle size reduction and isoniazid derivative synthesis and crystallization realized using sonocrystallization were investigated. The size, habit, structure, thermal behavior, and spectrometric properties of sonocrystallized crystals were analyzed through scanning electron microscopy (SEM), powder X-ray diffractometry (PXRD), differential scanning calorimetry (DSC), and Fourier transform infrared (FTIR) spectroscopy. The effects of the operating parameters, such as sonication intensity, sonication duration, and solution concentration, on sonocrystallization were compared. The crystal size of salicylamide was reduced from 595 µm (the original size) and was efficiently manipulated to be between 40 and 80 µm. Moreover, compared with the crystal habits of unprocessed crystals and recrystallized crystals fabricated through conventional methods, the crystal habit of salicylamide could be modified to present a regular shape. The structure, thermal behavior, and spectrometric properties of sonocrystallized salicylamide were found to be in agreement with those of an unprocessed sample. For producing isoniazid derivative crystals, N-(propan-2-ylidene)-isonicotinohydrazide was synthesized using isoniazid in acetone at 318 K. The resulting solution was then cooled by applying power ultrasound to isolate N-(propan-2-ylidene)-isonicotinohydrazide crystals. The solid-state properties of the synthesized N-(propan-2-ylidene)-isonicotinohydrazide was verified through PXRD, DSC, and FTIR spectroscopy. The feasibility of particle size manipulation was then demonstrated through sonocrystallization.

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Section: Introductionmentioning

confidence: 99%

Sonocrystallization—Case Studies of Salicylamide Particle Size Reduction and Isoniazid Derivative Synthesis and Crystallization

Yang

Yen

et al. 2018

Crystals

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“…Furthermore, the formation of these multicomponent crystals does not lead to changes in the nature of the API, unlike the situation observed during salt formation, where the API must or may be protonated [4]. Co-crystals containing heterocyclic nitrogen bases have been studied extensively, especially those with mono-and di-carboxylic acids as co-formers, and it can be concluded that the interaction between a carboxylic acid and a pyridine is a supramolecular synthon of frequent use in crystal engineering that may exist as a cocrystal (CO 2 H• • • N) or as salt (CO 2 − • • • HN + ) [5][6][7][8][9]. However, few studies are known of cocrystals with carboxylic acids as co-formers that also contain a hydroxyl moiety [10], such as the α-hydroxycarboxylic acids, particularly against isonicotinic acid hydrazide (isoniazid, inh) (Scheme 1) as API.…”

Section: Introductionmentioning

confidence: 99%

Weak Interactions in Cocrystals of Isoniazid with Glycolic and Mandelic Acids

et al. 2021

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This work deals with the preparation of pyridine-3-carbohydrazide (isoniazid, inh) cocrystals with two α-hydroxycarboxylic acids. The interaction of glycolic acid (H2ga) or d,l-mandelic acid (H2ma) resulted in the formation of cocrystals or salts of composition (inh)·(H2ga) (1) and [Hinh]+[Hma]–·(H2ma) (2) when reacted with isoniazid. An N′-(propan-2-ylidene)isonicotinic hydrazide hemihydrate, (pinh)·1/2(H2O) (3), was also prepared by condensation of isoniazid with acetone in the presence of glycolic acid. These prepared compounds were well characterized by elemental analysis, and spectroscopic methods, and their three-dimensional molecular structure was determined by single crystal X-ray crystallography. Hydrogen bonds involving the carboxylic acid occur consistently with the pyridine ring N atom of the isoniazid and its derivatives. The remaining hydrogen-bonding sites on the isoniazid backbone vary based on the steric influences of the derivative group. These are contrasted in each of the molecular systems. Finally, Hirshfeld surface analysis and Density-functional theory (DFT) calculations (including NCIplot and QTAIM analyses) have been performed to further characterize and rationalize the non-covalent interactions.

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“…Trans-cinnamic acid derivatives have shown to augment the activity of various antibiotics against Mycobacterium avium [12] and also show antioxidant, anti-inflammatory and cytotoxic properties. [13] , [14] Cinnamic acid derivatives bearing phenolic hydroxyl groups also have free radical scavenging properties [15] , [16], and so may sacrificially reduce the chemical degradation of easily oxidized APIs, such as INH. Weakly basic drugs show decreased solubility and dissolution as pH increases from 1 to 7 along the gastrointestinal tract, which is detrimental to drug absorption.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and structural characterization of cocrystals of isoniazid and cinnamic acid derivatives

Mashhadi

Yufit

Liu

et al. 2020

Journal of Molecular Structure

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The hierarchies of hydrogen bonds in salts/cocrystals of isoniazid and its Schiff base – a case study

Abstract: A series of two salts of isoniazid and two cocrystals of its Schiff base have been synthesized and well characterized. Further, the hydrogen bonding patterns have been studied and the correlation between the bond distances and corresponding pKa's have been deduced.

Cited by 18 publications

References 49 publications

Sonocrystallization—Case Studies of Salicylamide Particle Size Reduction and Isoniazid Derivative Synthesis and Crystallization

Sonocrystallization—Case Studies of Salicylamide Particle Size Reduction and Isoniazid Derivative Synthesis and Crystallization

Weak Interactions in Cocrystals of Isoniazid with Glycolic and Mandelic Acids

Synthesis and structural characterization of cocrystals of isoniazid and cinnamic acid derivatives

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