Refine
Has Fulltext
- yes (2)
Is part of the Bibliography
- yes (2)
Year of publication
- 2012 (2) (remove)
Document Type
- Journal article (2)
Language
- English (2)
Keywords
- 2,5-diketopiperazines (1)
- R factor = 0.025 (1)
- T = 173 K (1)
- T cell (1)
- anti-proliferative effects (1)
- chemistry (1)
- data-to-parameter ratio = 14.6 (1)
- derivates (1)
- diketopiperazines (1)
- intramolecular Michael addition (1)
The title compound, \(C_{21}H_{21}O_2PS_2\), was obtained from the corresponding dilithio methandiide by treatment with iodo-methane. The bond lengths and angles deviate considerably from those in the dimetallated compound. These differences are most pronounced in the PCS backbone. While the title compound features C-P and C-S distances of 1.9082(17) and 1.8348(17)Å, respectively, the dianion showed \(C-P_{av}\) distances shortened by 11% [1.710(4)Å] and C-S distances shortened by 12% [1.614(3)Å]. Additionally, the P-C-S angle experiences a contraction by methyl-ation of the dianion from 121.4(2) to 111.96(9)° in the title compound.
The well-known Ugi reaction of aldehydes with amines, carboxylic acids and isocyanides leads to the formation of acyclic alpha-acylaminocarboxamides. Replacement of the carboxylic acid derivatives with beta-acyl substituted acrylic acids gives access to highly substituted 2,5-diketopiperazines in one single reaction-step without additives or complex reaction procedures. The obtained diketopiperazines show anti-proliferative effects on activated T cells and represent therefore potential candidates for targeting unwanted T cell-mediated immune responses.