𝔖 Bobbio Scriptorium
✦   LIBER   ✦

The preparation of specifically 2H-labeled benz[A]anthracenes and 7,12-dimethylbenz[A]anthracenes1

✍ Scribed by Richard K. Hallmark; Wayne B. Manning; Gary M. Muschik

Publisher
John Wiley and Sons
Year
1981
Tongue
French
Weight
537 KB
Volume
18
Category
Article
ISSN
0022-2135

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The 2 + 4 cycloaddition reaction of 1,4‐naphthoquinone and substituted styrenes was used to prepare 1‐, 2‐, 3‐, and 4‐bromobenz[a]anthracene‐7,12‐diones (BADs). The corresponding bromobenz[a]anthracenes (BAs) were prepared by aluminum tricyclohexoxide reduction of the diones. Lithiation with t‐butyllithium followed by quenching with deuterium oxide gave the specifically ^2^H‐labeled BAs with deuterium incorporations of >95%. The 2‐, 3‐, and 4‐bromo‐7,12‐dimethylbenz‐[a]anthracenes (DMBAs) were prepared from the bromo BADs in moderate yield by the classical Grignard procedure. Lithium aluminum deuteride reduction gave the ^2^H‐DMBAs. An alternate synthesis from 3,4‐dihydrobenz[a]anthracene 1‐(2H)‐one was used for the preparation of 1‐ and 2‐^2^H BAs and DMBAs.

📜 SIMILAR VOLUMES

A simple method for the synthesis of spe
A simple method for the synthesis of specific [2H] and [3H]labelled methyl-hydroxylated derivatives of 7,12-dimethylbenz[a]anthracene
✍ Peter P. Fu; Shen K. Yang 📂 Article 📅 1979 🏛 John Wiley and Sons 🌐 French ⚖ 316 KB

Specific [ ' H I and [ 3H] labelled methyl-hydroxylated derivatives of 7,12-dimethylbenz[a]anthracene (DMBA), 7-hydroxymethyl-12methylbenz[a]anthracene, 7-methyl-12-hydroxymethylbenz[a]anthracene, and 7,12-dihydroxymethylbenz[a]anthracene, were synthesized with good yield and high specific activity.

Syntheses of putative metabolites of 1,2
Syntheses of putative metabolites of 1,2,3,4-tetrahydro-7,12-dimethylbenz[a]anthracene
✍ Srivastava, Santosh K. ;Sharma, Pradeep K. 📂 Article 📅 1995 🏛 John Wiley and Sons 🌐 English ⚖ 427 KB

## Abstract Syntheses of (8α,9α,10α,11β)‐__trans__‐1,2,3,4,8,9,10,11‐octahydro‐7,12‐dimethyl‐8,9‐epoxybenz[a]anthracene‐10,11‐diol (3) and (8α,9α,10β,11α)‐__trans__‐1,2,3,4,8,9,10,11‐octahydro‐7,12‐dimethyl‐8,9‐epoxybenz[a]anthracene‐10,11‐diol (4), the putative D‐ring metabolites of 1,2,3,4‐tetrah

Analysis of the epoxide of 7,12-dimethyl
Analysis of the epoxide of 7,12-dimethylbenz(a)anthracene and its hydrolysis products by gas chromatography
✍ C.E. Morreal; T.L. Dao; A.J. Spiess 📂 Article 📅 1976 🏛 Elsevier Science 🌐 English ⚖ 455 KB

Column chromatography and electron-capture gas chromatography have been applied to the separation and quantitative analysis of the K-region epoxide of 7,12-dimethylbenz(a)anthracene, S-hydroxy-7,12-dimethylbenz(a)anthracene, and trans-5,6-dihydro-5,6-dihydroxy-7,12-dimethylbenz(a)anthracene. Deacti

Specific N-ras mutation in bone marrow w
Specific N-ras mutation in bone marrow within 48 H of 7,12-dimethylbenz[a]anthracene treatment in Huggins-Sugiyama rat leukemogenesis
✍ Mitsuhiko Osaka; Shinji Matsuo; Takashi Koh; Taketoshi Sugiyama 📂 Article 📅 1996 🏛 John Wiley and Sons 🌐 English ⚖ 836 KB

7,12-Dimethylbenz[a]anthracene (DMBA)-induced leukemias in Long-Evans rats consistently have an A+T transversion at the second base of codon 61 in the N-ras gene. This mutation is also detected in t h e preleukemic stage. To determine when this specific N-ras mutation occurs in the early stages of l