5-Fluoro-N′-[(E)-4-methoxybenzylidene]-3-phenyl-1H-indole-2-carbohydrazide

Akkurt, Mehmet; Çeli̇k, İsmail; Cihan, Gökçe; Çapan, Gültaze; Büyükgüngör, Orhan

doi:10.1107/s1600536810009098

Cited by 5 publications

(2 citation statements)

References 7 publications

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“…Regarding ctc-II (Figure 6a), this synthon is more anticipated, since, for example, it has been described in some solvates (such as BOKHIU, BOKHOA, BOKHUG, BOK-JAO), 43 a clathrate (WOPCIO), 44 and some monocomponent structures (such as KUVFIR 45 or NIGNEY 46 ).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Co-crystal of Tramadol Hydrochloride–Celecoxib (ctc): A Novel API–API Co-crystal for the Treatment of Pain

Almansa

MercÃ

Tesson³

et al. 2017

Crystal Growth & Design

129

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We have identified a co-crystal of tramadol hydrochloride−celecoxib (ctc; E-58425/MR308), a novel active pharmaceutical ingredient (API)−API co-crystal formed by an intrinsic 1:1 molecular ratio of rac-tramadol•HCl and celecoxib, which displays favorable physicochemical and dissolution profiles. Adequate treatment of pain represents an unmet medical need that is often addressed via combination therapy. API−API co-crystals represent a new approach with potential to improve physicochemical properties, bioavailability, stability, or formulation capacity, which may translate into optimized pharmacokinetic profiles and clinical benefits compared with individual APIs or their combination. ctc showed a well-defined differential scanning calorimetry profile, and its single-crystal X-ray diffraction structure demonstrated a supramolecular 3D network in which the two active enantiomers of tramadol and celecoxib are linked via hydrogen bonding and chloride ions. Oversaturation studies indicated that the saturation effect for highly insoluble celecoxib occurred at a higher concentration in ctc than in celecoxib alone. Comparative intrinsic dissolution rate studies showed that the release of celecoxib was faster, and the release of tramadol was slower, from ctc than from the individual APIs, predicting an improved pharmacokinetic behavior for ctc. Together with findings from preclinical studies, these data support the clinical development of ctc for the treatment of pain.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Co-crystal of Tramadol Hydrochloride–Celecoxib (ctc): A Novel API–API Co-crystal for the Treatment of Pain

Almansa

MercÃ

Tesson³

et al. 2017

Crystal Growth & Design

129

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“…EtOH, reflux, 5-6 h; (vi) mercaptoacetic acid, dry benzene, reflux, 5-6 h and (vii) 2-mercaptopropionic acid, dry benzene, reflux, 5-6 h. DOI: 10.3109/14756366.2015.1024673 ionization mass spectrometry (ESI-MS) and HPLC studies. The absolute stereochemistry of 6c was determined by an X-ray diffraction study 30 . The absence of the N-H 2 resonance of the intermediate hydrazide (5) (Figure 2).…”

Section: Chemistrymentioning

confidence: 99%

Indole-based hydrazide-hydrazones and 4-thiazolidinones: synthesis and evaluation as antitubercular and anticancer agents

Cihan-Üstündağ¹,

Şatana

Özhan

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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A new series of indolylhydrazones (6) and indole-based 4-thiazolidinones (7, 8) have been designed, synthesized and screened for in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv. 4-Thiazolidinone derivatives 7g-7j, 8g, 8h and 8j displayed notable antituberculosis (anti-TB) activity showing 99% inhibition at MIC values ranging from 6.25 to 25.0 mg/ml. Compounds 7g, 7h, 7i, 8h and 8j demonstrated anti-TB activity at concentrations 10-fold lower than those cytotoxic for the mammalian cell lines. The indolylhydrazone derivative 6b has also been evaluated for antiproliferative activity against human cancer cell lines at the National Cancer Institute (USA). Compound 6b showed an interesting anticancer profile against different human tumor-derived cell lines at sub-micromolar concentrations with obvious selectivity toward colon cancer cell line COLO 205.

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5-Chloro-N′-cyclohexylidene-3-methyl-1H-indole-2-carbohydrazide

et al. 2013

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Key indicators: single-crystal X-ray study; T = 296 K; mean (C-C) = 0.004 Å; R factor = 0.053; wR factor = 0.129; data-to-parameter ratio = 15.0.In the title compound, C 16 H 18 ClN 3 O, the cyclohexane ring adopts a distorted chair conformation. In the crystal, pairs of molecules are linked by N-HÁ Á ÁO hydrogen bonds into inversion dimers, forming R 2 2 (10) ring motifs. These dimers are connected through C-HÁ Á ÁN hydrogen bonds into chains along the a axis, forming layers parallel to (101). Related literature ExperimentalCrystal data

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5-Fluoro-N′-[(E)-4-methoxybenzylidene]-3-phenyl-1H-indole-2-carbohydrazide

Cited by 5 publications

References 7 publications

Co-crystal of Tramadol Hydrochloride–Celecoxib (ctc): A Novel API–API Co-crystal for the Treatment of Pain

Co-crystal of Tramadol Hydrochloride–Celecoxib (ctc): A Novel API–API Co-crystal for the Treatment of Pain

Indole-based hydrazide-hydrazones and 4-thiazolidinones: synthesis and evaluation as antitubercular and anticancer agents

5-Chloro-N′-cyclohexylidene-3-methyl-1H-indole-2-carbohydrazide

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