80360-23-2Relevant articles and documents
Efficient synthesis of acrylates bearing an aryl or heteroaryl moiety: One-pot method from aromatics and heteroaromatics using formylation and the horner-wadsworth-emmons reaction
Yasukata, Tatsuro,Matsuura, Takaharu
, p. 527 - 533 (2021/03/22)
Acrylates bearing an aryl or heteroaryl moiety were efficiently prepared by a one-pot process employing a sequence of lithiation, formylation and the Horner-Wadsworth-Emmons reaction starting from aromatic and heteroaromatic compounds. This method can efficiently introduce an acrylate moiety into aromatic and heteroaromatic compounds.
IMIDAZO-PYRIDINE COMPOUNDS AS PAD INHIBITORS
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, (2019/05/10)
Heterocyclic compounds of Formula (I), (II), and (III) are described herein along with their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof. The compounds described herein, their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof are PAD4 inhibitors and may be useful in the treatment of various disorders, for example rheumatoid arthritis, vasculitis, systemic lupus erythematosis, cutaneous lupus erythematosis, ulcerative colitis, cancer, cystic fibrosis, asthma, multiple sclerosis and psoriasis. The process of preparation of the compounds of Formula (I), (II), and (III), their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof, along with a pharmaceutical composition comprising a compound of Formula (I), Formula (II), Formula (III), or a pharmaceutically acceptable salt thereof have also been described.
Structural Optimization of Indole Derivatives Acting at Colchicine Binding Site as Potential Anticancer Agents
Hwang, Dong-Jin,Wang, Jin,Li, Wei,Miller, Duane D.
, p. 993 - 997 (2015/09/22)
A new series of indole analogues based on our earlier lead compound, 2-(1H-indol-5-yl)-4-(3,4,5-trimethoxyphenyl)-1H-imidazo[4,5-c]pyridine (42), was prepared as tubulin inhibitors in an effort to find a molecule with improved cytotoxic potency and metabo
Total synthesis of bouchardatine
Naik, Nilesh H.,Urmode, Tukaram D.,Sikder, Arun K.,Kusurkar, Radhika S.
, p. 1112 - 1114 (2013/09/24)
Two new, efficient and simple routes using Heck-type reaction and intramolecular cyclization were developed for the synthesis of the naturally occurring cytotoxic alkaloid 2-(4-oxo-3,4-dihydroquinazolin-2-yl)-1H-indole-3- carbaldehyde (bouchardatine).
Conformational, steric and electronic effects on the site- and chemoselectivity of the metal-catalyzed reaction of N-bis(trimethylsilyl)methyl, N-(2-indolyl)methyl α-diazoamides
Zhang, Bao,Wee, Andrew G. H.
, p. 4597 - 4608 (2012/07/28)
The Rh(ii)- and Cu(ii)-catalyzed reactions of N-bis(trimethylsilyl)methyl, N-(2-indolyl)methyl α-diazoamides are investigated to delineate how conformational, steric and electronic factors influence the site- and chemoselectivity of the metallocarbenoid r
Synthesis of 2-and 3-indolylpyrroles via 1,3-dipolar cycloadditions of muenchnones and nitroalkenes
Lopchuk, Justin M.,Gribble, Gordon W.
, p. 1617 - 1631 (2011/05/04)
A series of 2-and 3-indolylpyrroles were generated via 1,3-dipolar cycloadditions between (2-nitrovinyl)indoles and symmetrical and unsymmetrical 1,3-oxazolium-5-olates (muenchnones). The Japan Institute of Heterocyclic Chemistry.
Enhancement of chemically-induced HL-60 cell differentiation by 3,3′-diindolylmethane derivatives
Noguchi-Yachide, Tomomi,Tetsuhashi, Masashi,Aoyama, Hiroshi,Hashimoto, Yuichi
experimental part, p. 536 - 540 (2009/12/27)
3,3′-Diindolylmethane (DIM, 1) and its derivatives have been prepared, and their enhancing effects on chemically-induced HL-60 cell differentiation were analyzed. Among the prepared compounds, IndDIM (12) showed the most potent enhancing effect on HL-60 cell differentiation induced by chemicals, including retinoids, 1,25-dihydroxyvitamin D3, 12-O-tetradecanoyl phorbol-13-acetate and dimethyl sulfoxide.
4- And 5-aroylindoles as novel classes of potent antitubulin agents
Liou, Jing-Ping,Wu, Chang-Ying,Hsieh, Hsing-Pang,Chang, Chi-Yen,Chen, Chi-Ming,Kuo, Ching-Chuan,Chang, Jang-Yang
, p. 4548 - 4552 (2008/02/13)
A novel series of 4- and 5-aroylindole derivatives was prepared and evaluated for antitumor activity. Several compounds showed excellent antiproliferative activity as inhibitors of tubulin polymerization. Compounds 13,14,15, and 18, with IC50 v
Novel bis(1H-indol-2-yl)methanones as potent inhibitors of FLT3 and platelet-derived growth factor receptor tyrosine kinase
Mahboobi, Siavosh,Uecker, Andrea,Sellmer, Andreas,Cénac, Christophe,H?cher, Heymo,Pongratz, Herwig,Eichhorn, Emerich,Hufsky, Harald,Trümpler, Antje,Sicker, Marit,Heidel, Florian,Fischer, Thomas,Stocking, Carol,Elz, Sigurd,B?hmer, Frank-D.,Dove, Stefan
, p. 3101 - 3115 (2007/10/03)
FLT3 receptor tyrosine kinase is aberrantly active in many cases of acute myeloid leukemia (AML). Recently, bis(1H-indol-2-yl)methanones were found to inhibit FLT3 and PDGFR kinases. To optimize FLT3 activity and selectivity, 35 novel derivatives were synthesized and tested for inhibition of FLT3 and PDGFR autophosphorylation. The most potent FLT3 inhibitors 98 and 102 show IC 50 values of 0.06 and 0.04 μM, respectively, and 1 order of magnitude lower PDGFR inhibiting activity. The derivatives 76 and 82 are 20- to 40-fold PDGFR selective. Docking at the recent FLT3 structure suggests a bidentate binding mode with the backbone of Cys-694. Activity and selectivity can be related to interactions of one indole moiety with a Hydrophobic pocket including Phe-691, the only different binding site residue (PDGFR Thr-681). Compound 102 inhibited the proliferation of 32D cells expressing wildtype FLT3 or FLT3-ITD similarly as FLT3 autophosphorylation, and induced apoptosis in primary AML patient blasts.
4-Substituted D-glutamic acid analogues: The first potent inhibitors of glutamate racemase (MurI) enzyme with antibacterial activity
De Dios, Alfonso,Prieto, Lourdes,Martín, Jose Alfredo,Rubio, Almudena,Ezquerra, Jesus,Tebbe, Mark,López De Uralde, Beatriz,Martín, Justina,Sánchez, Ana,LeTourneau, Deborah L.,McGee, James E.,Boylan, Carole,Parr Jr., Thomas R.,Smith, Michele C.
, p. 4559 - 4570 (2007/10/03)
The first potent inhibitors of glutamate racemase (MurI) enzyme that show whole cell antibacterial activity are described. Optically pure 4-substituted D-glutamic acid analogues with (2R,4S) stereochemistry and bearing aryl-, heteroaryl-, cinnamyl-, or biaryl-methyl substituents represent a novel class of glutamate racemase inhibitors. Exploration of the D-Glu core led to the identification of lead compounds (-)-8 and 10. 2-Naphthylmethyl derivative 10 was found to be a potent competitive inhibitor of glutamate racemase activity (Ki = 16 nM, circular dichroism assay; IC50 = 0.1 μg/mL high-performance liquid chromatography (HPLC) assay). Thorough structure-activity relationship (SAR) studies led to benzothienyl derivatives such as 69 and 74 with increased potency (IC50 = 0.036 and 0.01 μg/mL, respectively, HPLC assay). These compounds showed potent whole cell antibacterial activity against S. pneumoniae PN-R6, and good correlation with the enzyme assay. Compounds 69, 74 and biaryl derivative 52 showed efficacy in an in vivo murine thigh infection model against Streptococcus pneumoniae. Data described herein suggest that glutamate racemase may be a viable target for developing new antibacterial agents.
