Synthesis of 1-amino-3-{2-[7-(6-deoxy-α/β-D-galactopyranos-6-YL) -1,7-dicarba-closo-dodecaboran(12)-1-YL]ethyl}cyclobutanecarboxylic acid hydrochloride

George Kabalka, Bhaskar C. Das, Sasmita Das, Guishing Li, Rajiv Srivastava, Nisha Natarajan, Muhammad K. Khan

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

1-Amino-3-{2-[7-(6-deoxy-α/β-D-galactopyranos- 6-yl)-1,7-dicarba-closo-dodecaboran(12)-1-yl]ethyl}cyclobutanecarboxylic acid was synthesized as a potential new agent for boron neutron capture therapy. The key step in the synthesis is the alkylation of 3-{2-[1,7-dicarba-closo-dodecaboran(12)-1-yl]ethyl}cyclobutanone ethylene monothioketal with 1,2:3,4-di-O-isopropylidene-6-O-triflyl-α-D-galactopyranose which gave the precursor ketone that was then converted to the title amino acid via a Bücherer-Strecker synthesis followed by removal of isopropylidene groups in HCl. Preliminary toxicity data in A 435 cancer cells were obtained.

Original languageEnglish (US)
Pages (from-to)836-842
Number of pages7
JournalCollection of Czechoslovak Chemical Communications
Volume67
Issue number6
DOIs
StatePublished - Jun 1 2002
Externally publishedYes

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Acids
Boron
Alkylation
Ketones
Galactose
Toxicity
Neutrons
Cells
Amino Acids
propylene
ethylene

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Synthesis of 1-amino-3-{2-[7-(6-deoxy-α/β-D-galactopyranos-6-YL) -1,7-dicarba-closo-dodecaboran(12)-1-YL]ethyl}cyclobutanecarboxylic acid hydrochloride. / Kabalka, George; Das, Bhaskar C.; Das, Sasmita; Li, Guishing; Srivastava, Rajiv; Natarajan, Nisha; Khan, Muhammad K.

In: Collection of Czechoslovak Chemical Communications, Vol. 67, No. 6, 01.06.2002, p. 836-842.

Research output: Contribution to journalArticle

Kabalka, George ; Das, Bhaskar C. ; Das, Sasmita ; Li, Guishing ; Srivastava, Rajiv ; Natarajan, Nisha ; Khan, Muhammad K. / Synthesis of 1-amino-3-{2-[7-(6-deoxy-α/β-D-galactopyranos-6-YL) -1,7-dicarba-closo-dodecaboran(12)-1-YL]ethyl}cyclobutanecarboxylic acid hydrochloride. In: Collection of Czechoslovak Chemical Communications. 2002 ; Vol. 67, No. 6. pp. 836-842.
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abstract = "1-Amino-3-{2-[7-(6-deoxy-α/β-D-galactopyranos- 6-yl)-1,7-dicarba-closo-dodecaboran(12)-1-yl]ethyl}cyclobutanecarboxylic acid was synthesized as a potential new agent for boron neutron capture therapy. The key step in the synthesis is the alkylation of 3-{2-[1,7-dicarba-closo-dodecaboran(12)-1-yl]ethyl}cyclobutanone ethylene monothioketal with 1,2:3,4-di-O-isopropylidene-6-O-triflyl-α-D-galactopyranose which gave the precursor ketone that was then converted to the title amino acid via a B{\"u}cherer-Strecker synthesis followed by removal of isopropylidene groups in HCl. Preliminary toxicity data in A 435 cancer cells were obtained.",
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AU - Kabalka, George

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