Literature DB >> 22822274

Facile Synthesis of Mutagen X (MX): 3-Chloro-4-(dichloromethyl)-5-hydroxy-5H-furan-2-one.

Venkata Velvadapu1, Mark E McDonnell, Eileen K Jaffe, Allen B Reitz.   

Abstract

3-Chloro-4-(dichloromethyl)-5-hydroxy-5H-furan-2-one (Mutagen X, MX) was synthesized in six steps from commercially-available and inexpensive starting materials (27% overall yield). This synthesis enables the preparation of MX analogs and does not require the use of chlorine gas, as do previously reported methods.

Entities:  

Year:  2012        PMID： 22822274      PMCID： PMC3398704          DOI： 10.1016/j.tetlet.2012.04.044

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  19 in total

1.  On the formation of mutagens in the chlorination of humic acid.

Authors:  K P Kringstad; P O Ljungquist; F De Sousa; L M Stroemberg
Journal:  Environ Sci Technol       Date:  1983-09       Impact factor: 9.028

Review 2.  Mutagenic compounds in chlorinated pulp bleaching waters and drinking waters.

Authors:  B Holmbom
Journal:  IARC Sci Publ       Date:  1990

3.  DNA strand breaks induced in cultured human and rodent cells by chlorohydroxyfuranones--mutagens isolated from drinking water.

Authors:  L W Chang; F B Daniel; A B DeAngelo
Journal:  Teratog Carcinog Mutagen       Date:  1991

Review 4.  Mutagenic effects of organic compounds in drinking water.

Authors:  J C Loper
Journal:  Mutat Res       Date:  1980-11       Impact factor: 2.433

5.  Vinyl chloride-induced DNA adducts. I: Quantitative determination of N2,3-ethenoguanine based on electrophore labeling.

Authors:  N Fedtke; J A Boucheron; M J Turner; J A Swenberg
Journal:  Carcinogenesis       Date:  1990-08       Impact factor: 4.944

6.  Reaction of the potent bacterial mutagen 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX) with 2'-deoxyadenosine and calf thymus DNA: identification of fluorescent propenoformyl derivatives.

Authors:  T Munter; F Le Curieux; R Sjöholm; L Kronberg
Journal:  Chem Res Toxicol       Date:  1998-03       Impact factor: 3.739

7.  First direct reductive amination of mucochloric acid: a simple and efficient method for preparing highly functionalized alpha,beta-unsaturated gamma-butyrolactams.

Authors:  Ji Zhang; Peter G Blazecka; James G Davidson
Journal:  Org Lett       Date:  2003-02-20       Impact factor: 6.005

8.  Mutagenicity and clastogenicity of 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX) in L5178Y/TK+/(-)-3.7.2C mouse lymphoma cells.

Authors:  K Harrington-Brock; C L Doerr; M M Moore
Journal:  Mutat Res       Date:  1995-11       Impact factor: 2.433

9.  The vinyl chloride-derived nucleoside, N2,3-ethenoguanosine, is a highly efficient mutagen in transcription.

Authors:  B Singer; S J Spengler; F Chavez; J T Kuśmierek
Journal:  Carcinogenesis       Date:  1987-05       Impact factor: 4.944

10.  Induction of gene mutation in mammalian cells by 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX), a chlorine disinfection by-product in drinking water.

Authors:  K Jansson; J M Hyttinen
Journal:  Mutat Res       Date:  1994-08       Impact factor: 2.433
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