Synthetic methodologies of achiral diarylmethanols, diaryl and triarylmethanes (TRAMs) and medicinal properties of diaryl and triarylmethanes-an overview

被引:236
作者
Mondal, Sankalan [1 ]
Panda, Gautam [1 ]
机构
[1] Cent Drug Res Inst, Med & Proc Chem Div, Lucknow 226001, Uttar Pradesh, India
关键词
CROSS-COUPLING REACTIONS; FRIEDEL-CRAFTS REACTION; ELECTRON-RICH ARENES; ONE-POT SYNTHESIS; NONSTEROIDAL AROMATASE INHIBITORS; PALLADIUM-CATALYZED ADDITION; HIGHLY SELECTIVE ALKYLATION; MAGNESIUM EXCHANGE-REACTION; DUAL-REAGENT CATALYSIS; BENZYLIC ZINC REAGENTS;
D O I
10.1039/c4ra01341g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The last decade has witnessed a high demand of various synthetic approaches towards bioactive achiral diarylmethanols, diaryl and triarylmethanes and the molecules derived thereof. Their biological and therapeutical relevancy in diverse areas such as antimicrobials, infectious, cardiovascular and nervous system disorders, genital tract diseases, estrogen related disorders and bone remodeling is quite well known. These small molecules have also been the starting materials for the development of a variety of pharmaceutically important compounds. Compounds belonging to this family have not only played a leading role in the development of small molecules as therapeutically useful compounds but also have become one of the mainstays for the development of organic synthesis. However, a comprehensive review which covers their synthesis as well as their biological activity is still lacking. (Two reviews cover the synthesis of chiral diarylmethanols through asymmetric aryl transfer, and three reviews cover the photochemical properties of triarylmethanes, bioconjugation, application of trityl ions and the use of triarylmethanes as dyes.) This review describes the synthesis as well as the biological activities of this group of molecules that came up in the last fifteen years (1995-2013). The current review will cover the various approaches followed for the synthesis of achiral diarylmethanols and the strategies followed for the synthesis of achiral diaryl as well as triarylmethanes. Finally, we will also cover the bioactivities of molecules containing the diaryl and triaryl methane core.
引用
收藏
页码:28317 / 28358
页数:42
相关论文
共 272 条
[1]   3,3′-Diindolylmethane (DIM) and its derivatives induce apoptosis in pancreatic cancer cells through endoplasmic reticulum stress-dependent upregulation of DR5 [J].
Abdelrahim, M ;
Newman, K ;
Vanderlaag, K ;
Samudio, I ;
Safe, S .
CARCINOGENESIS, 2006, 27 (04) :717-728
[2]   Synthesis of functionalized triarylmethanes based on a 'FeCl3-catalyzed benzylation/[3+3] cyclocondensation' strategy [J].
Ahmad, Rasheed ;
Riahi, Abdolmajid ;
Langer, Peter .
TETRAHEDRON LETTERS, 2009, 50 (13) :1490-1492
[3]   Triaryl methane derivatives as antiproliferative agents [J].
Al-Qawasmeh, RA ;
Lee, Y ;
Cao, MY ;
Gu, XP ;
Vassilakos, A ;
Wright, JA ;
Young, A .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (02) :347-350
[4]  
Alami M., 2009, Patent, Patent No. [WO/2009/147217 A1, 2009147217, 2009/147217 A1]
[5]   Understanding the behavior of N-tosyl and N-2-pyridylsulfonyl Imines in CuII-Catalyzed aza-friedel-crafts reactions [J].
Alonso, Ines ;
Esquivias, Jorge ;
Gomez-Arrayas, Ramon ;
Carretero, Juan C. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (16) :6401-6404
[6]   Synthesis of functionalised diarylmethanes via a cobalt-catalysed cross-coupling of arylzinc species with benzyl chlorides [J].
Amatore, Muriel ;
Gosmini, Corinne .
CHEMICAL COMMUNICATIONS, 2008, (40) :5019-5021
[7]   Silica Sulfuric Acid-promoted Deacylation of α-Bromo-β-diketones [J].
Aoyama, Tadashi ;
Kubota, Sho ;
Takido, Toshio ;
Kodomari, Mitsuo .
CHEMISTRY LETTERS, 2011, 40 (05) :484-485
[8]   Organolithium reagents bearing nonlinear optical chromophores. Synthesis of triarylmethane dyes [J].
Arbez-Gindre, C ;
Screttas, CG ;
Fiorini, C ;
Schmidt, C ;
Nunzi, JM .
TETRAHEDRON LETTERS, 1999, 40 (41) :7413-7416
[9]  
Arbiser J. L., 2010, International Patent, pA1, Patent No. [US 2010/0189762, 20100189762]
[10]   Palladium catalyzed ligand-free Suzuki cross-coupling reactions of benzylic halides with aryl boronic acids under mild conditions [J].
Bandgar, BP ;
Bettigeri, SV ;
Phopase, J .
TETRAHEDRON LETTERS, 2004, 45 (37) :6959-6962