Synthesis and bioactivities of novel piperidylpyrimidine derivatives: inhibitors of tumor necrosis factor-alpha production

Fujiwara, Norio; Fujita, Hitoshi; Iwai, Kiyotaka; Kurimoto, Ayumu; Murata, Shinobu; Kawakami, Hajime

doi:10.1016/s0960-894x(00)00227-4

Cited by 11 publications

(2 citation statements)

References 23 publications

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“…Veratric acid (3,4-dimethoxybenzoic acid, CAS Registry No. 93-07-2, Figure ) is an important pharmaceutical intermediate for preparation of several drugs, such as gefitinib, alfuzosin hydrochloride, inhibitors of tumor necrosis factor alpha production, and desleucyl glycopeptide antibiotics . Additionally, the fungistatic activity and antihypertensive and antioxidant bioactivities of veratric acid are reported in literature. , …”

Section: Introductionmentioning

confidence: 99%

Solubility of Veratric Acid in Eight Monosolvents and Ethanol + 1-Butanol at Various Temperatures

Tian

et al. 2013

J. Chem. Eng. Data

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The solubility of veratric acid (3,4-dimethoxybenzoic acid, with measured melting point of 453.12 K by differential scanning calorimetry, DSC) in eight monosolvents, including ethanol, 1-propanol, 2-propanol, 1-butanol, 2-methyl-1-propanol, methyl acetate, ethyl acetate, and 2-butanone, and binary mixtures of ethanol + 1-butanol was determined at (278 to 323) K and atmospheric pressure using a dynamic method. The modified Apelblat equation and two local composition models (NRTL and UNIQUAC) were used to correlate the solubility of veratric acid in pure solvents. The modified Apelblat and the Jouyban–Acree model were used to correlate the solute solubility in binary mixtures. A combination of the Jouyban–Acree model and van’t Hoff equation was used to predict solubility data in the mixed solvents at different temperatures and gives a reasonable prediction. Each of the correlation equations selected gives a good description of the relationship of solubility and the temperature, and correlated data of the modified Apelblat equation show the best agreement with the experimental data, with the overall relative average deviations values of 0.61 % and 0.62 % in pure solvents and binary mixtures, respectively.

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Section: Introductionmentioning

confidence: 99%

Solubility of Veratric Acid in Eight Monosolvents and Ethanol + 1-Butanol at Various Temperatures

Tian

et al. 2013

J. Chem. Eng. Data

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“…Removal of the protecting Boc group from 4a and 4b gave 5a and 5b , respectively, in high yield. The key step in the synthesis was the elaboration of the 2-aminoquinazoline heterocycle through a low-temperature (50 °C) fusion reaction of the HCl salts of 5a and 5b with an excess of cyanamide to yield the O-protected C-glycosides 6a and 6b , respectively. Deprotection of 6a and 6b using NaOMe in MeOH at room temperature (RT) afforded the desired 7 in 70% yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of C-Nucleosides Designed To Participate in Triplex Formation with Native DNA: Specific Recognition of an A:T Base Pair in DNA

Gold

2005

J. Org. Chem.

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[structure: see text] We have previously described a system of 2-aminoquinoline- and 2-aminoquinazoline-based C-deoxynucleosides (TRIPsides) that are designed to be incorporated into oligomers that can specifically bind in the major groove via Hoogsteen base pairing to any sequence of native DNA. The four TRIPsides are termed antiGC, antiCG, antiTA, and antiAT with respect to the Watson-Crick base pair targets that they bind. The first three TRIPsides have been prepared, characterized, and shown to form stable and sequence-specific triplexes. In the present study, we describe the preparation of two molecules, 2-amino-4-(2'-deoxy-beta-D-ribofuranosyl)quinazoline (7) and 2-amino-6-fluoro-4-(2'-deoxy-beta-D-ribofuranosyl)quinoline (14), that can serve as the remaining antiAT TRIPside. The phosphoramidites of 7 and 14 were prepared, but only the latter was successfully incorporated into DNA oligomers. It is demonstrated using UV-visible melting experiments that 14 forms sequence-specific intramolecular triplets with A:T base pairs at physiological pH.

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ChemInform Abstract: Synthesis and Bioactivities of Novel Piperidylpyrimidine Derivatives: Inhibitors of Tumor Necrosis Factor‐Alpha Production.

et al. 2000

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Synthesis and bioactivities of novel piperidylpyrimidine derivatives: inhibitors of tumor necrosis factor-alpha production

Cited by 11 publications

References 23 publications

Solubility of Veratric Acid in Eight Monosolvents and Ethanol + 1-Butanol at Various Temperatures

Solubility of Veratric Acid in Eight Monosolvents and Ethanol + 1-Butanol at Various Temperatures

Synthesis of C-Nucleosides Designed To Participate in Triplex Formation with Native DNA: Specific Recognition of an A:T Base Pair in DNA

ChemInform Abstract: Synthesis and Bioactivities of Novel Piperidylpyrimidine Derivatives: Inhibitors of Tumor Necrosis Factor‐Alpha Production.

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