5513-36-0

Upstream product

• 1142-20-7 N-Cbz-Ala 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 3401-36-3 (N-benzyloxycarbonyl)-L-alanine N-hydroxysuccinimide ester 
• 7284-37-9 D-glucopyranosyl amine 
• 125814-23-5 Z-L-Ala-NCA 

Relevant academic research and scientific papers

Regioselective reaction of unprotected sugars with urethane N-carboxyanhydrides for the synthesis of new surfactants

Reaction of urethane N-carboxyanhydrides with unprotected amino sugars was the key step in the synthesis of new trimodular surfactants.

In the search for new anticancer drugs. 27. Synthesis and comparison of anticancer activity in vivo of amino acids, carbohydrates, and carbohydrate- amino acid conjugates containing the [N'-(2-chloroethyl)-N'- nitrosoamino]carbonyl group

The [N'-(2-chloroethyl)-N'-nitrosoamino]carbonyl [(2- chloroethyl)nitrosocarbamoyl, CNC] moiety containing compounds CNC- glycinamide 2d, CNC-amino acid derivatives 7a-d, and carbohydrate-CNC-amino acid conjugates 13, 18, 22, 23, 27, and 28 were synthesized and evaluated in vivo for their anticancer activities against the murine lymphocytic leukemia P388 using the National Cancer Institute (NCI) protocol. The most active compound was 2d with a 520% increase in life span (%ILS) and 6/6 survivors after 60 days. The CNC-amino acid analogs 7a-d possessed high to moderate activities with maximum %ILS values of 270, 174, 141 and 132, respectively. Among the carbohydrate-CNC-amino acid derivatives the α-methyl glycoside derivatives 22 and 23 were most active with maximum %ILS values of 277 and 137, respectively, followed by the hemiacetal carbohydrate analogs 13 and 18 with %ILS values of 93 and 149, respectively, and the tetra-O-acetyl derivatives 27 and 28 with %ILS of 110 and 111, respectively. Compounds 7b, 18, 23 and 28 were then tested in vivo against the murine lymphoid leukemia L1210 using the NCI protocol. In this case, the hemiacetal type carbohydrate- CNC-amino analog 18 had the highest activity with a maximum %ILS value of 477 and 4/6 survivors on day 60, followed by 7b (275% ILS), 23 (152% ILS) and 28 (106% ILS). The lipophilicities of all CNC compounds were determined by the partition coefficient using the UV method. A correlation of %ILS values with log P values indicated, in general, an increase in cytotoxicity with a decrease in hydrophilicity for the carbohydrate-CNC-amino acid conjugates 13, 18, 22, 23 and the clinical drugs streptozotocin (1e), chlorozotocin (1f), and cymerin (1g).