151884-07-0Relevant articles and documents
A short synthesis of 7-amino alkoxy homoisoflavonoides
Asadipour, Ali,Pourshojaei, Yaghoub,Eskandari, Khalil,Foroumadi, Alireza
, p. 44680 - 44687 (2017)
The synthesis of novel derivatives of homoisoflavonoids as potentially interesting medicinally important heterocycles in an efficient catalytic two step route is introduced. In the first step, 7-aminoalkoxychromane-4-ones are synthesized via reaction between 7-hydroxychroman-4-one and aminoethylchlorides in the presence of potassium carbonate as a Br?nsted base catalyst. In the next step, obtained 7-aminoalkoxychromane-4-ones are reacted with a wide range of arylaldehydes in the presence of hydrochloric acid as Br?nsted acid catalyst to obtain homoisoflavonoids. Target products are medicinally very important heterocycles, because their analogs show cytotoxic activities towards human cancer cell lines.
Synthesis and Evaluation of Chroman-4-One Linked to N-Benzyl Pyridinium Derivatives as New Acetylcholinesterase Inhibitors
Arab, Saman,Sadat-Ebrahimi, Seyed-Esmail,Mohammadi-Khanaposhtani, Maryam,Moradi, Alireza,Nadri, Hamid,Mahdavi, Mohammad,Moghimi, Setareh,Asadi, Mehdi,Firoozpour, Loghman,Pirali-Hamedani, Morteza,Shafiee, Abbas,Foroumadi, Alireza
, p. 643 - 649 (2015)
A novel series of chroman-4-one derivatives containing the N-benzyl pyridinium moiety were designed, synthesized, and evaluated for their acetylcholinesterase (AChE) inhibitory activities. Among the various synthesized compounds, (E)-1-(2,3-dibromobenzyl)-4-((7-ethoxy-4-oxochroman-3-ylidene)methyl)pyridinium bromide (8l) depicted the most potent anti-AChE activity (IC50=0.048μM). In addition, the molecular modeling study allowed us to detect possible binding modes that are in full compliance with the observed results through in vitro experiments. A novel series of chroman-4-one derivatives bearing N-benzyl pyridinium derivatives (8a-l) were synthesized and evaluated in vitro for their acetylcholinesterase inhibitory activities. The most promising compound, (E)-1-(2,3-dibromobenzyl)-4-((7-ethoxy-4-oxochroman-3-ylidene)methyl)pyridinium bromide 8l, showed an IC50 value of 0.048μM.
Novel chromanone-dithiocarbamate hybrids as multifunctional AChE inhibitors with β-amyloid anti-aggregation properties for the treatment of Alzheimer's disease
Jiang, Neng,Ding, Jiaoli,Liu, Jing,Sun, Xiaona,Zhang, Zhipeng,Mo, Zhongxia,Li, Xiao,Yin, Hong,Tang, Weizhong,Xie, Sai-Sai
, (2019)
By connecting chromanone with dithiocarbamate moieties through flexible linkers, a series of hybrids as novel multifunctional AChE inhibitors have been designed and synthesized. Most of these compounds displayed strong and excellently selective inhibition
Asymmetric Transfer Hydrogenation of Arylidene-Substituted Chromanones and Tetralones Catalyzed by Noyori-Ikariya Ru(II) Complexes: One-Pot Reduction of C═C and C═O bonds
Caleffi, Guilherme S.,Brum, Juliana De O. C.,Costa, Angela T.,Domingos, Jorge L. O.,Costa, Paulo R. R.
, p. 4849 - 4858 (2021/04/06)
3-Arylidenechroman-4-ones and 2-arylidene-1-tetralones are hydrogenated to cis-benzylic alcohols in dr's and er's up to 99:1 via a C═C and C═O one-pot reduction in the presence of 2-5 mol % Noyori-Ikariya-type RuII chiral complexes and HCO2Na as a hydroge
The evaluation of 1-tetralone and 4-chromanone derivatives as inhibitors of monoamine oxidase
Cloete, Stephanus J.,N’Da, Clarina I.,Legoabe, Lesetja J.,Petzer, Anél,Petzer, Jacobus P.
, p. 491 - 507 (2020/10/02)
Abstract: Monoamine oxidase (MAO) is of much clinical relevance, and inhibitors of this enzyme are used in the treatment for neuropsychiatric and neurodegenerative disorders such as depression and Parkinson’s disease. The present study synthesises and evaluates the MAO inhibition properties of a series of 33 1-tetralone and 4-chromanone derivatives in an attempt to discover high-potency compounds and to expand on the structure–activity relationships of MAO inhibition by these classes. Among these series, eight submicromolar MAO-A inhibitors and 28 submicromolar MAO-B inhibitors are reported, with all compounds acting as specific inhibitors of the MAO-B isoform. The most potent inhibitor was a 1-tetralone derivative (1h) with IC50 values of 0.036 and 0.0011?μM for MAO-A and MAO-B, respectively. Interestingly, with the reduction of 1-tetralones to the corresponding alcohols, a decrease in MAO inhibition potency is observed. Among these 1-tetralol derivatives, 1p (IC50 = 0.785?μM) and 1o (IC50 = 0.0075?μM) were identified as particularly potent inhibitors of MAO-A and MAO-B, respectively. Potent compounds such as those reported here may act as leads for the future development of MAO-B specific inhibitors. Graphic abstract: The present study describes the MAO inhibitory activities of a series of 1-tetralone and 4-chromanone derivatives. Numerous high-potency MAO-B specific inhibitors were identified.[Figure not available: see fulltext.].
INHIBITORS OF ANTIGEN PRESENTATION BY HLA-DR
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Page/Page column 122, (2021/10/11)
Chromanone compounds, pharmaceutical compositions containing them, methods of making them, and methods of using them including methods for treating disease states, disorders, and conditions associated with the inhibition of antigen presentation by HLA-DR.
Vanadium-Catalyzed Oxidative Intramolecular Coupling of Tethered Phenols: Formation of Phenol-Dienone Products
Gilmartin, Philip H.,Kozlowski, Marisa C.
supporting information, p. 2914 - 2919 (2020/04/10)
A mild and efficient method for the vanadium-catalyzed intramolecular coupling of tethered free phenols is described. The corresponding phenol-dienone products are prepared directly in good yields with low catalyst loadings. Electronically diverse tethered phenol precursors are well tolerated, and the catalytic method was effectively applied as the key step in syntheses of three natural products and a synthetically useful morphinan alkaloid precursor.
Design, synthesis and biological evaluation of rasagiline-clorgyline hybrids as novel dual inhibitors of monoamine oxidase-B and amyloid-β aggregation against Alzheimer's disease
Cheng, Maojun,Guo, Jie,Jiang, Neng,Li, Qing,Liang, Ningsheng,Liu, Jing,Nong, Xiaojie,Pang, Chengyun,Qin, Yuelian,Tang, Chunli,Tang, Weizhong,Xie, Sai-Sai,Zhang, Zhipeng
, (2020/07/10)
A series of rasagiline-clorgyline hybrids was designed, synthesized and investigated in vitro for their inhibition of monoamine oxidase and amyloid-β aggregation. Most of compounds were found to be selective and highly potent hMAO-B inhibitors showing IC50 values in the nanomolar, and exhibited a moderate inhibition of amyloid-β aggregation. 7-((5-(methyl(prop-2-yn-1-yl)amino) pentyl)oxy)chroman-4-one (6j) was the most interesting compound identified in this research, endowed with higher hMAO-B potency (IC50 = 4 nM) and selectivity (SI > 25000) compared to the reference selective inhibitor rasagiline (IC50 = 141 nM, SI > 355), and exhibited good inhibitory activity against Aβ1-42 aggregation (40.78percent, 25 μM). Kinetic and molecular modeling studies revealed that 6j was a competitive reversible inhibitor for hMAO-B. Moreover, compound 6j displayed low toxicity and good neuroprotective effects in SH-SY5Y cell assay, and could penetrate the blood-brain barrier according to the parallel artificial membrane permeability assay. Pharmacokinetics assay revealed that compound 6j possessed good pharmacokinetic profiles after intravenous and oral administrations. Overall, these results highlighted that compound 6j was an effective and promising multitarget agent against Alzheimer's disease.
Chroman derivatives having estrogen receptor degradation activity and uses thereof
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Page/Page column 101; 103; 104; 107, (2020/11/27)
The present disclosure relates to novel compounds, pharmaceutical compositions containing such compounds, and their use in prevention and treatment of cancer and related diseases and conditions.
ALPHA, BETA-UNSATURATED AMIDE COMPOUND
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Paragraph 0548, (2020/12/10)
An object of the present invention is to provide an α,β-unsaturated amide compound or a pharmaceutically acceptable salt or the like thereof having anticancer activity and the like. The α,β-unsaturated amide compound represented by the following formula (I) or a pharmaceutically acceptable salt or the like thereof has anticancer activity and the like: [wherein, "A" represents optionally substituted heterocyclic diyl, R1 represents hydrogen atom or optionally substituted lower alkyl, R2 represents optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted aliphatic heterocyclic group or optionally substituted aromatic heterocyclic group, X represents -O-, -S-, -SO2-, -NRX1- (wherein, RX1 represents hydrogen atom or lower alkyl), -CHRX2- (wherein, RX2 represents hydrogen atom or hydroxy), -CH=CH-, -CO- or -NH-CO-, and n1 and n2 are the same or different, and each represents 0 or 1].
