α-取代γ-内酰胺的短程立体选择性合成
Short stereoselective synthesis of alpha-substituted gamma-lactams.
作者信息
Raghavan Bhooma, Johnson Rodney L
机构信息
Department of Medicinal Chemistry, University of Minnesota, 308 Harvard Street Southeast, Minneapolis, Minnesota 55455, USA.
出版信息
J Org Chem. 2006 Mar 3;71(5):2151-4. doi: 10.1021/jo052212q.
Abstract
A concise, stereoselective synthesis of alpha-substituted gamma-lactams is reported. gamma-Lactam scaffolds 2 and 3, possessing an Evans' chiral auxiliary and two types of N substituents, were successfully alkylated with different electrophiles to give alpha-substituted gamma-lactams with reasonable diastereoselectivities. The use of a masked carboxymethyl function off the lactam nitrogen provided a convergent means to alpha-substituted gamma-lactam dipeptide isosteres.
摘要
报道了一种简洁的、立体选择性合成α-取代γ-内酰胺的方法。具有伊文斯手性助剂和两种类型N取代基的γ-内酰胺支架2和3，成功地与不同的亲电试剂进行烷基化反应，以合理的非对映选择性得到α-取代γ-内酰胺。在γ-内酰胺氮上使用掩蔽的羧甲基官能团为合成α-取代γ-内酰胺二肽类似物提供了一种汇聚方法。
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本文引用的文献
1
Synthesis and dopamine receptor modulating activity of 3-substituted gamma-lactam peptidomimetics of L-prolyl-L-leucyl-glycinamide.L-脯氨酰-L-亮氨酰-甘氨酰胺的3-取代γ-内酰胺肽模拟物的合成及多巴胺受体调节活性
J Med Chem. 2003 Feb 27;46(5):727-33. doi: 10.1021/jm020441o.
2
Structure-based design, synthesis and evaluation of conformationally constrained cysteine protease inhibitors.基于结构的构象受限半胱氨酸蛋白酶抑制剂的设计、合成与评价
Bioorg Med Chem. 1998 Dec;6(12):2477-94. doi: 10.1016/s0968-0896(98)80022-9.
3
Synthesis and dopamine receptor modulating activity of lactam conformationally constrained analogues of Pro-Leu-Gly-NH2.脯氨酸-亮氨酸-甘氨酸-酰胺（Pro-Leu-Gly-NH2）的内酰胺构象受限类似物的合成及其对多巴胺受体的调节活性
J Med Chem. 1993 Jan 22;36(2):256-63. doi: 10.1021/jm00054a010.
4
Dopamine receptor modulation by conformationally constrained analogues of Pro-Leu-Gly-NH2.脯氨酸-亮氨酸-甘氨酸-酰胺（Pro-Leu-Gly-NH2）构象受限类似物对多巴胺受体的调节作用
J Med Chem. 1988 Jul;31(7):1430-6. doi: 10.1021/jm00402a031.
5
Conformationally constrained renin inhibitory peptides: gamma-lactam-bridged dipeptide isostere as conformational restriction.
J Med Chem. 1988 Jul;31(7):1369-76. doi: 10.1021/jm00402a021.
6
Synthesis and antiinflammatory activities of 3-(3,5-di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-ones.3-(3,5-二叔丁基-4-羟基亚苄基)吡咯烷-2-酮的合成与抗炎活性
J Med Chem. 1987 Nov;30(11):1995-8. doi: 10.1021/jm00394a011.
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