Rearrangements of N-Oxides. A Novel Synthesis of Pyridyl Carbinols and Aldehydes

Boekelheide, V.; Linn, W. J.

doi:10.1021/ja01634a026

Cited by 277 publications

(84 citation statements)

References 3 publications

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“…2-Picoline-N-oxide resulted from peracetic acid oxidation of 2-picoline (10). Oxidation of 9-nzethylanthracene.-9-NIethyla11thracene (0.95 g.) in carbon tetrachloride (80 ml.)…”

Section: Methodsmentioning

confidence: 99%

Étard Reaction: Ii. Polycyclic Aromatic and Heterocyclic Compounds

Wheeler¹

1958

Can. J. Chem.

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“…2-Picoline-N-oxide resulted from peracetic acid oxidation of 2-picoline (10). Oxidation of 9-nzethylanthracene.-9-NIethyla11thracene (0.95 g.) in carbon tetrachloride (80 ml.)…”

Section: Methodsmentioning

confidence: 99%

Étard Reaction: Ii. Polycyclic Aromatic and Heterocyclic Compounds

Wheeler¹

1958

Can. J. Chem.

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“…[34] Solution of 3/4 (19 mmol) was added to acetic anhydride (40 mL) and was heated at reflux for 4 h. After cooling, excess acetic anhydride was evaporated under reduced pressure (high-vacuum oil pump) to obtain black crude. The resulting syrup was purified by silica gel column (petroleum ether/EtOAc/MeOH 10:30:60).…”

Section: -Carboxy-nn-dimethylpropan-1-amine Oxide (S-3)mentioning

confidence: 99%

A Chemical Chaperone‐Based Drug Candidate is Effective in a Mouse Model of Amyotrophic Lateral Sclerosis (ALS)

et al. 2015

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Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative disease characterized by the selective death of motor neurons and skeletal muscle atrophy. The majority of ALS cases are acquired spontaneously, with inherited disease accounting for only 10 % of all cases. Recent studies provide compelling evidence that aggregates of misfolded proteins underlie both types of ALS. Small molecules such as artificial chaperones can prevent or even reverse the aggregation of proteins associated with various human diseases. However, their very high active concentration (micromolar range) severely limits their utility as drugs. We synthesized several ester and amide derivatives of chemical chaperones. The lead compound 14, 3-((5-((4,6-dimethylpyridin-2-yl)methoxy)-5-oxopentanoyl)oxy)-N,N-dimethylpropan-1-amine oxide shows, in the micromolar concentration range, both neuronal and astrocyte protective effects in vitro; at daily doses of 10 mg kg(-1) 14 improved the neurological functions and delayed body weight loss in ALS mice. Members of this new chemical chaperone derivative class are strong candidates for the development of new drugs for ALS patients.

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“…Dieses reagierte rnit Acetanhydrid in einer Boekelheide-Umlagerung 14) zum 2-Pyridylmethylacetat 10a. Alkalische Esterverseifung lieferte den Alkohol lla, der sich rnit SOCl2 zur Chlormethylverbindung 12a umsetzte.…”

Section: Synthesewege Zu Pyrido[32-e][14]diazepinenunclassified

Pyrido[3,2‐e][1,4] diazepine ‐ Synthese und Prüfung auf Anti‐HIV‐1‐Wirkung

Görlitzer

Wilpert

Rübsamen‐Waigmann

et al. 1995

Archiv der Pharmazie

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Starting from the commercially available 6-methyl-2-pyridylamine (1) the pyrido[3,2-e][1,4]diazepine 14a was synthesized in 12 steps with 7% total yield. 14a, the N-methyl derivative 14b, the thiolactam 15a, the amidine 16, and the 1,2,4-triazole 17 were tested for anti-HIV-1-activity. None of the compounds tested possesses antiviral activity comparable to that of zidovudine (3'-azido-3'-desoxythymidine = AZT).

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Rearrangements of N-Oxides. A Novel Synthesis of Pyridyl Carbinols and Aldehydes

Cited by 277 publications

References 3 publications

Étard Reaction: Ii. Polycyclic Aromatic and Heterocyclic Compounds

Étard Reaction: Ii. Polycyclic Aromatic and Heterocyclic Compounds

A Chemical Chaperone‐Based Drug Candidate is Effective in a Mouse Model of Amyotrophic Lateral Sclerosis (ALS)

Pyrido[3,2‐e][1,4] diazepine ‐ Synthese und Prüfung auf Anti‐HIV‐1‐Wirkung

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