4005-49-6Relevant articles and documents
Cycloalkane analogues of sinefungin as EHMT1/2 inhibitors
Liu, Qing,Cai, Xiaoqing,Yang, Dehua,Chen, Yi,Wang, Yafang,Shao, Liming,Wang, Ming-Wei
, p. 4579 - 4594 (2017/10/05)
A series of cycloalkyl substituted analogues of the natural product sinefungin lacking the amino-acid moiety was designed and synthesized. Two stereoisomers (6-R and 6-S) were separated and their bioactivities examined against EHMT1/2. Of which, compound 14d showed an inhibitory activity against EHMT1/2 (88.9%, IC50 = 21.8 μM for EHMT1 and 77.6%, IC50 = 39.6 μM for EHMT2, respectively) similar to that of sinefungin (100.0%, IC50 = 28.4 μM for EHMT1 and 79.5%, IC50 = 30.1 μM for EHMT2, respectively). Further studies against other methyltransferases such as PRMT1 showed no activity except that 12d displayed about 20% inhibition.
Structure-activity relationship study of N N6-benzoyladenine-type BRD4 inhibitors and their effects on cell differentiation and TNF-α production
Amemiya, Seika,Yamaguchi, Takao,Sakai, Taki,Hashimoto, Yuichi,Noguchi-Yachide, Tomomi
, p. 1378 - 1383 (2016/09/09)
Bromodomains are epigenetic 'readers' of histone acetylation. The first potent bromodomain and extra-terminal domain (BET) inhibitors, (+)-JQ1 and I-BET762 (also known as GSK525762), were reported in 2010. Some BET inhibitors are already under clinical trial for the treatment of cancers, but so far, only a few chemical scaffolds are available. We have reported potent N N6-benzoyladenine-based inhibitors of BRD4, a BET family member that serves as a key mediator of transcriptional elongation. Here we present an analysis of the structure-activity relationships of these inhibitors. Among the compounds examined, 20, 28 and 29 enhanced all-trans retinoic acid (ATRA)-induced HL-60 cell differentiation and inhibited tumor necrosis factor (TNF)-α production by THP-1 cells.
PEPTIDE NUCLEIC ACID MONOMERS AND OLIGOMERS
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, (2011/10/13)
Disclosed is a peptide nucleic acid monomer as well as a corresponding peptide nucleic acid molecule. The monomer comprises a terminal amino group and a terminal group A. The terminal amino group and the terminal group A are connected by an aliphatic moie
Microwave-assisted synthesis of amides from various amines and benzoyl chloride under solvent-free conditions: A rapid and efficient method for selective protection of diverse amines
Li, Yanqiu,Wang, Yulu,Wang, Jinye
, p. 358 - 361 (2008/12/22)
A number of structurally diverse amides were synthesized by reaction of the corresponding amines with benzoyl chloride under microwave irradiation. The proposed procedure ensures short reaction time, high yields, and excellent selectivity and considerably broadens the series of amines as compared to the microwave-assisted synthesis of amides directly from carboxylic acids. It can also be used for selective protection of various amines, including aromatic, aliphatic, and heterocyclic.
Microwave-promoted conversion of heterocyclic amines to corresponding amides under solvent-free conditions
Li, Yanqiu,Wang, Yulu,Wang, Jinye
, p. 251 - 256 (2008/03/14)
An array of heterocyclic amides was synthesized efficiently by combining corresponding amines and benzoyl chloride in one-pot under microwave irradiation. The reaction times were shorter, yields were higher. What is more, the regioselectivity was excellent, which made the protocol support us an entry to selective protection of diverse amino groups.
Design, development and synthesis of a novel labeled PNA monomer incorporated in DNA-hexamer to act as a hybridization probe by FRET
Shukla, Vibha,Mishra, Satyendra,Watal, Geeta,Misra, Krishna
, p. 121 - 129 (2007/10/03)
A novel PNA monomer with adenine nucleobase and a modified backbone with charged -N+-H and a methylene substituted for 2 bond on the lefthand side sign C=O in the linker arm has been synthesised. This modified PNA monomer is further linked with
Novel and efficient syntheses of 3′,5′-diamino derivatives of 2′,3′,5′-trideoxycytidine and 2′,3′,5′-trideoxyadenosine. Protonation behavior of 3′,5′-diaminonucleosides
Lavandera, Iván,Fernández, Susana,Ferrero, Miguel,Gotor, Vicente
, p. 5449 - 5456 (2007/10/03)
High yielding synthetic routes to 3′,5′-diamino-2′,3′,5′-trideoxycytidine and 3′,5′-diamino-2′,3′,5′-trideoxyadenosine are described. In addition, the protonation behavior of 3′,5′-diamino-2′,3′,5′-trideoxycytidine, 3′,5′-diamino-2′,3′,5′-trideoxyadenosin
Studies on the mechanism of ribonucleotide reductases
Lenz, Roman,Giese, Bernd
, p. 2784 - 2794 (2007/10/03)
Ribonucleotide reductases are enzymes that catalyze the conversion of ribonucleotides to 2'-deoxyribonucleotides. This important reaction is initiated by the generation of a C-3' nucleotide radical and subsequent loss of the 2'-hydroxyl group. In order to model certain steps in this mechanism, selenol ester 23 was prepared and photolyzed providing the first selective chemical access to the 3'-adenosyl radical. From product analysis it could be shown that elimination of the 2'-OH function readily takes place under general base catalysis. The rate coefficient for this reaction was determined by competition kinetics to be 1.5 · 106 s-1 in the presence of 1 M triethylammonium acetate buffer at pH 7. Without catalyst the elimination rate is about 103 times slower. It can be concluded that a similar mechanism is also feasible for the key steps of the enzyme catalyzed reaction.
Preparation of 1′-c deuterated synthons for RNA synthesis by H-phosphonate method aiming at two-dimensional NMR secondary structure studies
Arnold, Lubos,Pressova, Martina,Saman, David,Vogtherr, Martin,Limmer, Stefan
, p. 389 - 403 (2007/10/03)
1′-C Deuterated H-phosphonate synthons were prepared via a 12-step procedure starting from [1′-2H]ribose. The procedure included nucleosidation of 1′-O-acetyl-2′,3′,5'-O-tribenzoyl[1′- 2H]ribose with appropriately protected nucleobases and preparation of nucleoside-H-phosphonates by slightly modified described procedures. The automated RNA synthesis of 5′-G* C*U*A*U*UUAU-3′ and 3′-AC* G*A*U*A*AAGU-5′ was performed on a Gene Assembler Plus DNA-synthesizer. These specifically deuterated oligoribonucleotides were subsequently compared with the corresponding nondeuterated sequences using 2D-NMR NOESY spectra. Specific deuterium incorporation resulted in the expected simplification of spectral pattern.
Ozonolysis of 6-N-Benzoyl-9-(5-deoxy-2,3-O-isopropylidene-β-D-erythro-pent-4-enofuranosyl)adenine and Relateds Compounds
Joshi, Bhalchandra V.,Reese, Colin B.
, p. 5807 - 5810 (2007/10/02)
The nucleoside 4',5'-olefins 3, 5, 7 and 9 are readily converted into the corresponding lactones 4, 6, 8 and 10, respectively, by ozonolysis in dichloromethane solution at -78 deg C.
