Synthesis of 3′-Aminopteroic Acid

Wells, Jack N.; Strahl, M.S.

doi:10.1002/jps.2600600403

Cited by 10 publications

(2 citation statements)

References 17 publications

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“…Deuterium incorporation into C^-DBCP and C3D2-DBCP was greater than 95 atom % as determined by analysis of the (M -Br)+ species (at m/z 155-162) generated by electron impact mass spectrometry; the deuterated analogues were >98% chemically pure by gas chromatographic analysis. 2-Bromoacrolein was prepared by triethylamine-catalyzed dehydrobromination of 2,3-dibromopropanal (19) and purified to >98% by vacuum distillation. 1-Chloropropene was purchased from K and K Laboratories (Plainview, NY); 1-bromopropene, m-chloroperoxybenzoic acid, dimethyl sulfoxide, and TV-bromosuccininide were obtained from Aldrich Chemical Co. (Milwaukee, WI).…”

Section: Methodsmentioning

confidence: 99%

“…Residual 1-chloropropene and CC14 were removed by distillation (76-78 °C at atmospheric pressure). The product was purified by vacuum distillation (32-34 °C at 6 mmHg) to afford 5.9 g (38.6 mmol, yield = 29.4%) of the Zand E-isomers of l-chloro-3-bromopropene, in a ratio of 60:40, respectively: *H NMR (CDC13, 300 MHz) [(Z)-l-chloro-3-bromopropene] 6.23 (1 H, d, 7 Hz, ClffCCHCH2Br), 6.12 (1 H, m, ClHCCHCH2Br), and 4.05 (2 H, d, 7 Hz, ClHCCHCH2Br); [(E)-l-chloro-3-bromopropene] 6.35 (1 H, dt, 13 and 1 Hz, ClHCCHCH2Br), 6.16 (1 H, m, ClHCCtfCH2Br), and 3.95 (2 H, d, 7 Hz, ClHCCHCH2Br); EI-MS m/z (% relative intensity) 158 (M'+, 5), 156 (M*+, 19), 154 (M*+, 16), 77 (M*+ -Br, 38), 75 (M'+ -Br, 100).…”

Section: Methodsmentioning

confidence: 99%

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Metabolic activation of 1,2-dibromo-3-chloropropane to mutagenic metabolites: detection and mechanism of formation of (Z)- and (E)-2-chloro-3-(bromomethyl) oxirane

Pearson

Omichinski

Myers

et al. 1990

Chem. Res. Toxicol.

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1,2-Dibromo-3-chloropropane (DBCP), a haloalkane nematocide and soil fumigant, is metabolically activated to chemically reactive species that are direct-acting mutagens in a Salmonella typhimurium TA 100 test system. Studies in vitro with rat liver microsomes indicated that oxidation at carbon 3 resulted in the formation of an unstable gem-chlorohydrin that rearranged with elimination of hydrogen bromide to form (Z)-2-chloro-3-(bromomethyl)oxirane [(Z)-CBPO] and (E)-2-chloro-3-(bromomethyl)oxirane [(E)-CBPO]. Gas chromatography-mass spectrometry (GC-MS) with positive ion chemical ionization (CI) was employed to identify (Z)-CBPO and (E)-CBPO by comparison of characteristic fragment ions in their CI mass spectra with those observed for authentic standards. Quantitative GC-MS methodology was exploited to quantitate the rate of formation of (Z)-CBPO and (E)-CBPO from DBCP and analogues of DBCP specifically deuterated at carbon 1 and carbon 3. The rate of formation of Z- and E-isomers of CBPO was 31 and 33 pmol/(min.mg of protein), respectively, from DBCP; substitution with deuterium at carbon 1 increased the rate of epoxide formation by 50%, whereas CBPO formation could not be detected from a substrate labeled with deuterium at carbon 3. Both epoxides were directly acting mutagens to S. typhimurium TA 100. (Z)-CBPO caused approximately twice as many his+ revertants/nmol compared to (E)-CBPO. Oxidation at carbon 2 of DBCP resulted in the formation of a bifunctional alkylating agent, 1-bromo-3-chloroacetone, presumably via the intermediacy of an unstable gem-bromohydrin.(ABSTRACT TRUNCATED AT 250 WORDS)

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Metabolic activation of 1,2-dibromo-3-chloropropane to mutagenic metabolites: detection and mechanism of formation of (Z)- and (E)-2-chloro-3-(bromomethyl) oxirane

Pearson

Omichinski

Myers

et al. 1990

Chem. Res. Toxicol.

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References

1988

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Darstellung, Struktur und Reaktionen der Halogenmalondialdehyde

Reichardt

Halbritter

1975

Angewandte Chemie

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In diesem Fortschrittsbericht wird ein Uberblick iiber Synthese, Struktur und Reaktionen von Halogenmalondialdehyden einschlieljlich des ,,Cyanmalondialdehyds" (Diformylacetonitrils) gegeben, der einzigen bisher bekannten Pseudohalogenverbindung dieser Reihe. Charakteristisch fur die reaktiven und vielseitig venvendbaren Halogenmalondialdehyde sind vor allem ihre Cyclisierungsreaktionen mit bifunktionellen Verbindungen. Viele der hier besprochenen Reaktionen lassen sich auch auf andere substituierte Malondialdehyde iibertragen. EinfarungWahrend gesZttigte aliphatische Dialdehyde der allgemeinen Formel OCH-(CH2),--CH0 (n> 1) im Vergleich zu einfachen Monoaldehyden in ihrem chemischen Verhalten nichts grundlegend Neues bieten und sich wie bifunktionelle Monoaldehyde verhalten, bilden Glyoxal (n = 0) und Malondialdehyd (n = l), die ersten Glieder dieser homologen Reihe, eine Ausnahme, da bei ihnen die beiden Carbonylgruppen in konjugativer Wechselwirkung stehen bnv.

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Synthesis of 3′-Aminopteroic Acid

Cited by 10 publications

References 17 publications

Metabolic activation of 1,2-dibromo-3-chloropropane to mutagenic metabolites: detection and mechanism of formation of (Z)- and (E)-2-chloro-3-(bromomethyl) oxirane

Metabolic activation of 1,2-dibromo-3-chloropropane to mutagenic metabolites: detection and mechanism of formation of (Z)- and (E)-2-chloro-3-(bromomethyl) oxirane

References

Darstellung, Struktur und Reaktionen der Halogenmalondialdehyde

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