Maize 1:  A Trimorphic Azo Pigment

Price, Christopher P.; Grzesiak, Adam L.; Kampf, Jeff W.; Matzger, Adam J.

doi:10.1021/cg025610k

Cited by 22 publications

(8 citation statements)

References 30 publications

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“…Crystal polymorphism can have a profound effect on solid‐state properties and, because of potential differences in bioavailablity, is of key importance in the manufacture of drugs. Traditional methods of controlling the phenomenon of polymorphism,4–6 including modification of crystallization conditions, such as changing solvent, temperature of crystallization, extent of supersaturation, or melt crystallization, are often not efficient at discovering new polymorphs or controlling phase production. However, several recent methods have proven effective in selective production of known forms 7–17.…”

Section: Introductionmentioning

confidence: 99%

New form discovery for the analgesics flurbiprofen and sulindac facilitated by polymer‐induced heteronucleation

Grzesiak¹,

Matzger²

2007

Journal of Pharmaceutical Sciences

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The selection and discovery of new crystalline forms is a longstanding issue in solid-state chemistry of critical importance because of the effect molecular packing arrangement exerts on materials properties. Polymer-induced heteronucleation has recently been developed as a powerful approach to discover and control the production of crystal modifications based on the insoluble polymer heteronucleant added to the crystallization solution. The selective nucleation and discovery of new crystal forms of the well-studied pharmaceuticals flurbiprofen (FBP) and sulindac (SUL) has been achieved utilizing this approach. For the first time, FBP form III was produced in bulk quantities and its crystal structure was also determined. Furthermore, a novel 3:2 FBP:H 2 O phase was discovered that nucleates selectively from only a few polymers. Crystallization of SUL in the presence of insoluble polymers facilitated the growth of form I single crystals suitable for structure determination. Additionally, a new SUL polymorph (form IV) was discovered by this method. The crystal forms of FBP and SUL are characterized by Raman and FTIR spectroscopies, X-ray diffraction, and differential scanning calorimetry.

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Section: Introductionmentioning

confidence: 99%

New form discovery for the analgesics flurbiprofen and sulindac facilitated by polymer‐induced heteronucleation

Grzesiak¹,

Matzger²

2007

Journal of Pharmaceutical Sciences

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“…Table 1 shows the aromatic diazonium salt as a route to new azines and condensed azines with potential activities. Therefore, 1 coupled smoothly with the aromatic diazonium salt to yield the corresponding arylhydrazones, 6a – c in good yield [ 24 ]. However, the condensation of 1 with the aromatic aldehydes in a basic medium afforded the arylidine derivatives, 7a , b [ 25 ].…”

Section: Resultsmentioning

confidence: 99%

Multifunctional Isosteric Pyridine Analogs-Based 2-Aminothiazole: Design, Synthesis, and Potential Phosphodiesterase-5 Inhibitory Activity

et al. 2021

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The elaboration of new small molecules that target phosphodiesterase enzymes (PDEs), especially those of type 5 (PDE5), is an interesting and emerging topic nowadays. A new series of heterocycle-based aminothiazoles were designed and synthesized from the key intermediate, 3-oxo-N-(thiazol-2-yl)butanamide (a PDE5 inhibitor that retains its amidic function), as an essential pharmacophoric moiety. The PDE5 inhibitors prevent the degradation of cyclic guanosine monophosphate, thereby causing severe hypotension as a marked side effect. Hence, an in vivo testing of the target compounds was conducted to verify its relation with arterial blood pressure. Utilizing sildenafil as the reference drug, Compounds 5, 10a, and 11b achieved 100% inhibitions of PDE5 without significantly lowering the mean arterial blood pressures (115.95 ± 2.91, 110.3 ± 2.84, and 78.3 ± 2.57, respectively). The molecular docking study revealed that the tested compounds exhibited docking poses that were similar to that of sildenafil (exploiting the amide functionality that interacted with GLN:817:A). The molecular shape and electrostatic similarity revealed a comparable physically achievable electrostatic potential with the reference drug, sildenafil. Therefore, these concomitant results revealed that the tested compounds exerted sildenafil-like inhibitory effects (although without its known drawbacks) on blood circulation, thus suggesting that the tested compounds might represent a cornerstone of beneficial drug candidates for the safe treatment for erectile dysfunction.

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“…20,21 There is no doubt that the need to control polymorph formation is an important issue in the chemical industry. 22 Sometimes, the term "polymorph" could be used broadly, including both the amorphous state and solvates. [23][24][25][26][27][28] Solvates can be further subdivided into two main classes: stoichiometric and non-stoichiometric solvates.…”

Section: Introductionmentioning

confidence: 99%

Versatile solid modifications of icariin: structure, properties and form transformation

et al. 2015

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A comprehensive solid-state screening experiment was performed for icariin (ICA), an active substance in Traditional Chinese Medicine (TCM) which has long been used to treat osteroporosis. Two new polymorphs in their pure forms and ten different solvate modifications were obtained and the single crystal structures were successfully determined. The isostructural phenomenon was readily observed among various organic solvates. Notably, the single crystal structure of the marketed hydrate form H1 was determined for the first time through a single crystal-single crystal transformation (SCSCT) process. The physicochemical properties of various solid forms were further studied. The results show that the newly discovered pure form α presents better thermal stability, lower hygroscopicity and higher solubility compared to the currently marketed form. The superior physicochemical properties render a better drug development ability for this widely applied TCM.

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Maize 1: A Trimorphic Azo Pigment

Cited by 22 publications

References 30 publications

New form discovery for the analgesics flurbiprofen and sulindac facilitated by polymer‐induced heteronucleation

New form discovery for the analgesics flurbiprofen and sulindac facilitated by polymer‐induced heteronucleation

Multifunctional Isosteric Pyridine Analogs-Based 2-Aminothiazole: Design, Synthesis, and Potential Phosphodiesterase-5 Inhibitory Activity

Versatile solid modifications of icariin: structure, properties and form transformation

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