Investigating how amine structure influences drug-amine ion-pair formation and uptake via the polyamine transporter in A549 lung cells

Synthesis, X-ray Crystal Structure, and Computational Characterization of Tetraphenylborate, 3-(5H-Dibenzo[a,d] cyclohepten-5-ylidene)-N, N-Dimethyl-1-propanamine

“…Resonance peaks for N-CH2-CH2, N-(CH3)2, N-CH2-CH2, and N-CH2-CH2CH were observed at 24.47, 42.57, 56.61, and 122.33 ppm in the 13 C NMR spectra. The olefinic ethylene in the cyclobenzaprine ring manifests as two distinctive 1 H resonances, with intrinsic splitting patterns at around 6.92 and 6.80 ppm, and a resonance peak at 131.18 ppm in the 13 C NMR spectra. The tetraphenylboric ring's aromatic protons appeared in the 7.15-7.45 ppm range.…”

“…1 H NMR (700 MHz, DMSO_d6) δ: 2.2 (m, 2H, CH 2 ), 2.6 (s, 6H, N-CH 3 ), 3.0 (m, 2H, CH 2 ), 5.4 (t, J = 7.0 Hz, 1H, CH), 6.80 (d, J = 7.0 Hz, 1H, CH), 6.92 (d, J = 7.0 Hz, 1H, CH), 7.15 -7.45 (all, ArH). 13 C NMR δ: 24.55, 42.31, 56.56, 122.33, 126.13, 127.83, 128.10, 128.73, 128.97, 129.18, 129.41, 129.79, 131.18, 131.36, 131.60, 134.11, 134.33, 136.24, 136.38, 141.69, 144.49, 152.15, 163.30, 163.69, 164.10. Elemental analysis: (C44H41BN); cal.…”

“…The tetraphenylboric ring's aromatic protons appeared in the 7.15-7.45 ppm range. The IR spectrum of the target complex was characterized by the appearance of the absorption band 13 C NMR spectra. The olefinic ethylene in the cyclobenzaprine ring manifests as two distinctive 1 H resonances, with intrinsic splitting patterns at around 6.92 and 6.80 ppm, and a resonance peak at 131.18 ppm in the 13 C NMR spectra.…”

“…The IR spectrum of the target complex was characterized by the appearance of the absorption band 13 C NMR spectra. The olefinic ethylene in the cyclobenzaprine ring manifests as two distinctive 1 H resonances, with intrinsic splitting patterns at around 6.92 and 6.80 ppm, and a resonance peak at 131.18 ppm in the 13 C NMR spectra. The tetraphenylboric ring's aromatic protons appeared in the 7.15-7.45 ppm range.…”

“…One of the key advantages of employing drugs that form ion-pair complexes is that the active ingredient does not go through structural changes, making the medication more stable [10], have a longer half-life, and be more bioavailable [11,12]. Meanwhile, the creation of an ion-pair medicine results in a brand-new drug with improved absorption properties [13,14].…”