Approaches to Iodinated Derivatives of Vanillin and Isovanillin

Nammalwar, Baskar; Bunce, Richard A.; Berlin, K. Darrell; Bourne, Philip C.; Barrow, Esther W.; Barrow, William W.

doi:10.1080/00304948.2012.643700

Cited by 6 publications

(6 citation statements)

References 16 publications

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“…Benzaldehydes 6-9 , derived from 5-iodovanillin, were prepared using methodology previously described. 20 Condensation of 6 - 9 with 3-morpholinopropionitrile ( 10 ) using sodium methoxide in dry DMSO gave adducts 11 - 14 , which were treated sequentially in dry EtOH with aniline hydrochloride and guanidine hydrochloride, both in the presence of sodium methoxide, to afford the substituted 2,4-diamino-5-benzyl-1,3-pyrimidines 15 - 18 in 72-80% yields. Heck coupling of 15 - 18 with 3a and 3b then generated the target compounds 19a - b , 20a-b , 21a and 22a in 70-78% yields.…”

Section: Resultsmentioning

confidence: 99%

“…20 Sodium methoxide promoted condensation of 10 with 23 produced 24 , which was cyclocondensed with aniline hydrochloride and guanidine hydrochloride to give the substituted 2,4-diamino-5-benzyl-1,3-pyrimidine 25 in 83% yield. Heck coupling of 25 with 3a gave the MOM-protected catechol 26 , which was deprotected using methanolic hydrogen chloride to give phenol 27 (58%).…”

Section: Resultsmentioning

confidence: 99%

“…These compounds were prepared on a 54-mmol scale via a two-step literature procedure 20 in the following yields: 6 (80%), 7 (92%), 8 (92%), 9 (78%) and 23 (88%). The spectral data matched those reported.…”

Section: Methodsmentioning

confidence: 99%

“…This compound was prepared as described above for compound 15 using 23 20 (10.0 g, 24.0 mmol), 10 (4.03 g, 28.8 mmol, 1.2 equiv) and NaOMe (1.30 g, 24.0 mmol, 1.0 equiv) in DMSO (40 mL) to give intermediate 24 (9.24 g, 90%) as a dark brown oil. This oil in ethanol (150 mL) was treated with PhNH 2 ·HCl (3.10 g, 24.0 mmol, 1.0 equiv), guanidine·HCl (5.50 g, 57.6 mmol, 2.4 equiv), and NaOMe (5.18 g, 96.0 mmol, 4.0 equiv) to afford a dark yellow solution.…”

Section: Methodsmentioning

confidence: 99%

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Modified 2,4-diaminopyrimidine-based dihydrofolate reductase inhibitors as potential drug scaffolds against Bacillus anthracis

Nammalwar

Wakeham

Bourne

et al. 2015

Bioorganic & Medicinal Chemistry

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The current paper describes the synthesis and biological evaluation of dihydrophthalazine-appended 2,4-diaminopyrimidine (DAP) inhibitors (1) oxidized at the methylene bridge linking the DAP ring to the central aromatic ring and (2) modified at the central ring ether groups. Structures 4a-b incorporating an oxidized methylene bridge showed a decrease in activity, while slightly larger alkyl groups (CH2CH3 versus CH3) on the central ring oxygen atoms (R2 and R3) had a minimal impact on the inhibition. Comparison of the potency data for previously reported RAB1 and BN-53 with the most potent of the new derivatives (19b and 20a-b) showed similar values for inhibition of cellular growth and direct enzymatic inhibition (MICs 0.5-2 μg/mL). Compounds 29-34 with larger ester and ether groups containing substituted aromatic rings at R3 exhibited slightly reduced activity (MICs 2-16 μg/mL). One explanation for this attenuated activity could be encroachment of the extended R3 into the neighboring NADPH co-factor. These results indicate that modest additions to the central ring oxygen atoms are well tolerated, while larger modifications have the potential to act as dual-site inhibitors of dihydrofolate reductase (DHFR).

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Modified 2,4-diaminopyrimidine-based dihydrofolate reductase inhibitors as potential drug scaffolds against Bacillus anthracis

Nammalwar

Wakeham

Bourne

et al. 2015

Bioorganic & Medicinal Chemistry

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“…180 ℃); 1 H NMR (400 MHz, CDCl 3 ) δ: 9.80 (s, 1H), 7.72 (d, J＝1.6 Hz, 1H), 7.40 (d, J＝1.6 Hz, 1H), 4.00 (s, 3H). [23,24] : m.p. 198～199 ℃); 1 H NMR (400 MHz, CDCl 3 ) δ: 9.66 (s, 1H), 7.22 (s, 1H), 6.85 (s, 1H).…”

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confidence: 99%

Studies on the Synthesis of 5-Trifluoromethylpiperonal

Wang¹,

Han²,

Zhang³

et al. 2013

Chin. J. Org. Chem.

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5-Trifluoromethylpiperonal was obtained by iodination, demethylation, methylene etherification and trifluoromethyl reaction of vanillin in a satisfied yield. The chemical structure of the product was identified by 1 H NMR, 13 C NMR, 19 F NMR and HRMS. The optimal reaction conditions were investigated, including trifluoromethylation reagents, solvents, catalyst amounts, reaction temperature and reaction time. Meanwhile, three hydroxy substituted derivatives of 3,4-dihydroxy-5-iodo-benzaldehyde were acquired by trifluoromethylation reaction with this method.

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