环状砜-3-甲酰胺作为基于Ro 31-8959的HIV-1蛋白酶抑制剂的新型P-配体
CYCLIC SULFONE-3-CARBOXAMIDES AS NOVEL P-LIGANDS FOR Ro 31-8959 BASED HIV-1 PROTEASE INHIBITORS.
作者信息
Ghosh Arun K, Thompson Wayne J, Munson Peter M, Liut Wenming, Huff Joel R
机构信息
Department of Chemistry, University of IUinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607.
Department of Medicinal Chemistry, Merck Research Laboratories, West Point, PA 19486.
出版信息
Bioorg Med Chem Lett. 1995 Jan 5;5(1):83-88. doi: 10.1016/0960-894X(94)00463-P. Epub 2000 Mar 29.
Abstract
Cyclic sulfone-3-carboxamides are effective P-1igands for HIV-1 protease inhibitors. Incorporation of 3S-tetrahydro-2H-thiopyrancarboxamide-l, l-dioxide in the hydroxyethylamine series resulted in inhibitor (IC=9 nM, CIC=200 nM) with improved potency compared to its corresponding urethane derivative (IC=2.0 μM).
摘要
环状砜-3-羧酰胺是有效的HIV-1蛋白酶抑制剂的P配体。在羟乙胺系列中引入3S-四氢-2H-硫代吡喃甲酰胺-1,1-二氧化物，得到的抑制剂（IC = 9 nM，CIC = 200 nM）与相应的氨基甲酸酯衍生物（IC = 2.0 μM）相比，活性有所提高。
相似文献
1
CYCLIC SULFONE-3-CARBOXAMIDES AS NOVEL P-LIGANDS FOR Ro 31-8959 BASED HIV-1 PROTEASE INHIBITORS.环状砜-3-甲酰胺作为基于Ro 31-8959的HIV-1蛋白酶抑制剂的新型P-配体
Bioorg Med Chem Lett. 1995 Jan 5;5(1):83-88. doi: 10.1016/0960-894X(94)00463-P. Epub 2000 Mar 29.
2
Nonpeptidal P2 ligands for HIV protease inhibitors: structure-based design, synthesis, and biological evaluation.用于HIV蛋白酶抑制剂的非肽类P2配体：基于结构的设计、合成及生物学评价。
J Med Chem. 1996 Aug 16;39(17):3278-90. doi: 10.1021/jm960128k.
3
Discovery of HIV-1 protease inhibitors with picomolar affinities incorporating N-aryl-oxazolidinone-5-carboxamides as novel P2 ligands.发现具有皮摩尔亲和力的HIV-1蛋白酶抑制剂，其包含N-芳基-恶唑烷酮-5-甲酰胺作为新型P2配体。
J Med Chem. 2006 Dec 14;49(25):7342-56. doi: 10.1021/jm060666p.
4
Potent human immunodeficiency virus type 1 protease inhibitors that utilize noncoded D-amino acids as P2/P3 ligands.
J Med Chem. 1996 Jan 5;39(1):96-108. doi: 10.1021/jm950576c.
5
Design and synthesis of potent HIV-1 protease inhibitors incorporating hydroxyprolinamides as novel P2 ligands.设计并合成了强效的 HIV-1 蛋白酶抑制剂，其中包含羟脯氨酰胺作为新型 P2 配体。
Bioorg Med Chem Lett. 2011 Jun 15;21(12):3730-3. doi: 10.1016/j.bmcl.2011.04.070. Epub 2011 Apr 24.
6
Design and synthesis of highly potent HIV-1 protease inhibitors with novel isosorbide-derived P2 ligands.设计并合成具有新型异山梨醇衍生 P2 配体的高效抗 HIV-1 蛋白酶抑制剂。
Bioorg Med Chem Lett. 2014 Jun 1;24(11):2465-8. doi: 10.1016/j.bmcl.2014.04.008. Epub 2014 Apr 13.
7
Design and synthesis of potent HIV-1 protease inhibitors with (S)-tetrahydrofuran-tertiary amine-acetamide as P2-ligand: Structure-activity studies and biological evaluation.以 (S)-四氢呋喃-叔胺-乙酰胺为 P2 配体的高效 HIV-1 蛋白酶抑制剂的设计与合成：结构活性研究与生物学评价。
Eur J Med Chem. 2017 Sep 8;137:30-44. doi: 10.1016/j.ejmech.2017.05.024. Epub 2017 May 8.
8
Synthesis and biological evaluation of novel HIV-1 protease inhibitors using tertiary amine as P2-ligands.以叔胺作为P2配体的新型HIV-1蛋白酶抑制剂的合成及生物学评价
Bioorg Med Chem Lett. 2015 May 1;25(9):1880-3. doi: 10.1016/j.bmcl.2015.03.047. Epub 2015 Mar 24.
9
A comparison of cyclohexanone and tetrahydro-4H-thiopyran-4-one 1,1-dioxide as pharmacophores for the design of peptide-based inhibitors of the serine protease plasmin.环己酮和四氢-4H-硫代吡喃-4-酮1,1-二氧化物作为用于设计丝氨酸蛋白酶纤溶酶的肽基抑制剂的药效基团的比较。
J Org Chem. 2005 Oct 14;70(21):8309-21. doi: 10.1021/jo0508954.
10
A novel, picomolar inhibitor of human immunodeficiency virus type 1 protease.一种新型的、皮摩尔级的1型人类免疫缺陷病毒蛋白酶抑制剂。
J Med Chem. 1996 Jan 19;39(2):392-7. doi: 10.1021/jm9507183.
引用本文的文献
1
Beyond darunavir: recent development of next generation HIV-1 protease inhibitors to combat drug resistance.超越达芦那韦：新一代 HIV-1 蛋白酶抑制剂抵抗耐药性的最新进展。
Chem Commun (Camb). 2022 Oct 20;58(84):11762-11782. doi: 10.1039/d2cc04541a.
2
Asymmetric Aldol Route to Hydroxyethylamine Isostere: Stereoselective Synthesis of the Core Unit of Saquinavir.通往羟乙胺电子等排体的不对称羟醛缩合路线：沙奎那韦核心单元的立体选择性合成。
J Org Chem. 1997 Aug 22;62(17):6080-6082. doi: 10.1021/jo9706943.
3
Chiral Auxiliary Mediated Conjugate Reduction and Asymmetric Protonation: Synthesis of High Affinity Ligands for HIV Protease Inhibitors.手性助剂介导的共轭还原和不对称质子化：HIV蛋白酶抑制剂高亲和力配体的合成
J Org Chem. 1995 Sep 1;60(19):6198-6201. doi: 10.1021/jo00124a042.
4
Harnessing nature's insight: design of aspartyl protease inhibitors from treatment of drug-resistant HIV to Alzheimer's disease.利用自然的智慧：从耐药性艾滋病毒治疗到阿尔茨海默病的天冬氨酰蛋白酶抑制剂设计
J Med Chem. 2009 Apr 23;52(8):2163-76. doi: 10.1021/jm900064c.
本文引用的文献
1
Tetrahydrothiophene (thiophane) derivatives.四氢噻吩（噻吩烷）衍生物
J Am Chem Soc. 1946 Nov;68(11):2229-35. doi: 10.1021/ja01215a034.
2
Cyclic sulfolanes as novel and high affinity P2 ligands for HIV-1 protease inhibitors.环丁砜作为新型高亲和力P2配体用于HIV-1蛋白酶抑制剂
J Med Chem. 1993 Apr 2;36(7):924-7. doi: 10.1021/jm00059a019.
3
3-Tetrahydrofuran and pyran urethanes as high-affinity P2-ligands for HIV-1 protease inhibitors.
J Med Chem. 1993 Jan 22;36(2):292-4. doi: 10.1021/jm00054a015.
4
The development of cyclic sulfolanes as novel and high-affinity P2 ligands for HIV-1 protease inhibitors.
J Med Chem. 1994 Apr 15;37(8):1177-88. doi: 10.1021/jm00034a016.
5
Affinity purification of the HIV-1 protease.HIV-1蛋白酶的亲和纯化
Biochem Biophys Res Commun. 1989 Nov 15;164(3):955-60. doi: 10.1016/0006-291x(89)91762-2.
6
Rational design of peptide-based HIV proteinase inhibitors.基于肽的HIV蛋白酶抑制剂的合理设计。
Science. 1990 Apr 20;248(4953):358-61. doi: 10.1126/science.2183354.
7
Synthesis and antiviral activity of a series of HIV-1 protease inhibitors with functionality tethered to the P1 or P1' phenyl substituents: X-ray crystal structure assisted design.
J Med Chem. 1992 May 15;35(10):1685-701. doi: 10.1021/jm00088a003.
Zotero 插件