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

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Title: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
Creators:
Kabalka, George W.
Das, Bhaskar C.
Das, Sasmita
Li, Guishing
Srivastava, Rajiv
Natarajan, Nisha
Khan, Muhammad K.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 67, 6, pp. 836-842
Uncontrolled Keywords:Amino acids, BNCT, Carboranes, Boron neutron capture therapy, Carbohydrates

Abstract

1-Amino-3-{2-[7-(6-deoxy-α/β-D-galactopyranos-6-yl)-1,7-dicarba-<i>closo</i>-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-<i>closo</i>-dodecaboran(12)-1-yl]ethyl}cyclobutanone ethylene monothioketal with 1,2:3,4-di-<i>O</i>-isopropylidene-6-<i>O</i>-triflyl-α-D-galactopyranose which gave the precursor ketone that was then converted to the title amino acid <i>via</i> a Bücherer-Strecker synthesis followed by removal of isopropylidene groups in HCl. Preliminary toxicity data in A 435 cancer cells were obtained. <p>

Title: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
Creators:
Kabalka, George W.
Das, Bhaskar C.
Das, Sasmita
Li, Guishing
Srivastava, Rajiv
Natarajan, Nisha
Khan, Muhammad K.
Uncontrolled Keywords:Amino acids, BNCT, Carboranes, Boron neutron capture therapy, Carbohydrates
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:67
Number:6
Page Range:pp. 836-842
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20020836UNSPECIFIED
ID Code:1960
Item Type:Article
Deposited On:06 Feb 2009 17:14
Last Modified:06 Feb 2009 16:14

Citation

Kabalka, George W.; Das, Bhaskar C.; Das, Sasmita; Li, Guishing; Srivastava, Rajiv; Natarajan, Nisha; Khan, Muhammad K. (2002) 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. Collection of Czechoslovak Chemical Communications, 67 (6). pp. 836-842. ISSN 0010-0765

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