22824-31-3Relevant academic research and scientific papers
Wittig-Horner-Emmons reactions of triethyl 3-methyl-phosphonocrotonate with 3-formylchroniones en route to benzophenone-based retinoid candidates
Sun, Weilin,Desai, Shyam,Piao, Huri,Carroll, Patrick,Canney, Daniel J.
, p. 557 - 567 (2007)
Wittig-Horner-Emmons (WHE) reaction conditions were used in conjunction with other reactions to prepare benzophenone-based retinoid candidates. The chromone nucleus was reacted with triethyl 3-methyl-phosphonocrotonate to afford benzophenones following a known rearrangement of a reaction intermediate. Confirmations of the structure of rearranged products are provided in the form of the X-ray crystal structures and speculation regarding the mechanism for the rearrangements is included. The method provides a facile route to substituted benzophenone-based candidate ligands for retinoic acid receptors (RARs) or for a wide variety of other applications.
Designed Spiroketal Protein Modulation
Scheepstra, Marcel,Andrei, Sebastian A.,Unver, M. Yagiz,Hirsch, Anna K. H.,Leysen, Seppe,Ottmann, Christian,Brunsveld, Luc,Milroy, Lech-Gustav
, p. 5480 - 5484 (2017)
Spiroketals are structural motifs found in many biologically active natural products, which has stimulated considerable efforts toward their synthesis and interest in their use as drug lead compounds. Despite this, the use of spiroketals, and especially b
Anticancer effects of synthetic hexahydrobenzo [g]chromen-4-one derivatives on human breast cancer cell lines
Pordeli, Mahboobeh,Nakhjiri, Maryam,Safavi, Maliheh,Ardestani, Sussan Kabudanian,Foroumadi, Alireza
, p. 299 - 311 (2017)
Background: Cancer results from a series of molecular changes that alter the normal function of cells. Breast cancer is the second leading cause of cancer death in women. To develop novel anticancer agents, new series of chromen derivatives were synthesized and evaluated for their cytotoxic activity against human breast cancer cell lines. Method: The growth inhibitory activities of synthesized hexahydrobenzo chromen-4-one were screened against six human cancer cell lines using an in vitro cell culture system (MTT assay). Fluorochrome staining (acridine orange/ethidium bromide double staining) and DNA fragmentation by the diphenylamine method were used to investigate the effects of most potent compounds on the process of apoptosis in breast cancer cell lines. To determine the mechanism of apoptosis, ROS and NOX production in treated breast cancer cells with compounds was evaluated. Results: The cytotoxicity data of tested compounds demonstrate these compounds had varying degree of toxicity. Compound 7h was the most potent compound with IC50?=?1.8?±?0.6?μg/mL against T-47D cell line. Analyses of the compounds treated (MCF-7, MDA-MB-231, and T-47D) cells by acridine orange/ethidium bromide double staining and DNA fragmentation by the diphenylamine method showed that the synthetic compounds induce apoptosis in the cells. A significant increase in ROS production was observed in T-47D cells treated with IC50 value of compound 7g. Incubation with IC50 value of synthetic compounds increased the NOX production in cell lines, especially T-47D cells. Conclusion: Our results show that most compounds have a significant anti-proliferative activity against six human cancer cell lines. The observations confirm that chromen derivatives have induced the cell death through apoptosis.
A Modular Approach to Dibenzo-fused ?-Lactams: Palladium-Catalyzed Bridging-C?H Activation
Huang, Xueliang,Ma, Liyao,Xia, Jiajin,Xin, Luoting,Yu, Yinghua,Zhu, Lei
supporting information, p. 18261 - 18266 (2020/08/21)
Tricyclic ring systems possessing a dibenzo structure joined to a seven-membered heterocyclic ring frequently show important biological activities. However, a modular approach to these molecules based on efficient intermolecular reaction of readily available chemicals is lacking. Herein, an unprecedented palladium-catalyzed formal [4+3] annulation for modular construction of these tricyclic systems is described. This reaction features easily accessible reactants (o-haloarylaldehydes and N-tosylhydrazones), broad substrate scope, and excellent functional group compatibility. The synthetic potential is demonstrated by the easy scale-up reactions, late-stage modification of complex molecules, and collective synthesis of bioactive molecules and approved drugs.
METHOD FOR PRODUCING AN ARENE WITH AN AROMATIC C-N BOND ORTHO TO AN AROMATIC C-O BOND
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Paragraph 0350; 0351, (2017/03/28)
A method for producing an arene with an aromatic C—N bond ortho to an aromatic C—O bond from a hydroxy arene comprising said aromatic C—O bond is provided. This method comprising the steps a) ortho-oxygenating the hydroxy arene to produce an ortho-quinone, b) condensating the ortho-quinone with a nitrogen nucleophile to generate a compound of Formula (IVa) or (IVb), and c) allowing 1,5-hydrogen atom shift of the compound of Formula (IVa) or (IVb), thereby producing arenes with a C—N bond ortho to a C—O bond of Formula (Va) and (Vb), respectively:
Bioisosteric replacement and related analogs in the design, synthesis and evaluation of ligands for muscarinic acetylcholine receptors
Bhandare, Richie R.,Canney, Daniel J.
, p. 361 - 375 (2014/05/20)
Previous structure-activity relationship studies involving a series of lactone-based muscarinic ligands identified a lead compound containing a diphenylmethylpiperazine moiety (4; IC50 = 340 nM). The purpose of the present work is to investigate 1,3-benzodioxoles, 4,4-diethyl substituted tetrahydrofurans, 5-substituted oxazolidinones and chromones as bioisosteric replacements for the lactone ring in a novel series of muscarinic ligands. The approach provided compounds with improved % inhibition values and identified a non-selective muscarinic ligand with an IC50 value of 280 nM. The structure-activity relationship for this new series will be discussed. Selected compounds were evaluated in preliminary assays for subtype selectivity and were found to be non-selective.
THERAPEUTIC DRUG FOR ADULT T-CELL LEUKEMIA
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Page/Page column 6, (2011/08/02)
An object is to provide a novel therapeutic drug for adult T-cell leukemia having an ATL cell specific antitumor effect. The therapeutic drug for adult T-cell leukemia according to the invention is characterized by containing a compound represented by the formula I or a prodrug thereof, wherein R1 is H, OH, an alkoxy group, an acyl group, or a thioacyl group, R2 is an acyl group, a thioacyl group, CONR7R8, or CSNR7R8 (R7 and R8 being each independently H, an alkyl group containing 1 to 3 carbon atoms, or a phenyl group), or R1 and R2 together may form a ring, X1 and X2 may be the same or different and are each —CR3R4—, —SiR3R4— or oxygen, and R3 and R4 may be the same or different and are each an alkyl group containing 1 to 6 carbon atoms.
SUBSTITUTED DIHYDRO BENZOCYCLOALKYLOXYMETHYL OXAZOLOPYRIMIDINONES, PREPARATION AND USE THEREOF
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Page/Page column 26-27, (2011/04/19)
The present invention relates to a series of substituted dihydro benzocycloalkyl-oxymethyl oxazolopyrimidinones of formula (I) as defined herein. This invention also relates to methods of making these compounds including novel intermediates. The compounds
Heterocycle-bridged and conformationally constrained retinoids: Synthesis of 4-(7,8,9,10-Tetrahydro-7,7,10,10-tetramethyl-4H-benzo[6,7]chromeno-[4,3-d]thiazole-2-yl)benzoic acid
Lamei, Navid,Foroumadi, Alireza,Emami, Saeed,Amini, Mohsen,Shafiee, Abbas
experimental part, p. 1951 - 1956 (2011/06/19)
Retinoids are a class of synthetic and natural compounds structurally related to retinoic acid. In a search for discovery of a new class of heterocycle-bridged and conformationally constrained retinoids, here we report the synthesis of 4-(7,8,9,10-tetrahydro-7,7,10,10-tetramethyl-4H-benzo[6,7]chromeno[4,3-d]thiazole-2-yl)benzoic acid (10) starting from 5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-ol (13). Several approaches was attempted to obtain target compound 10. Structure elucidation of synthesized compounds has been made on the basis of elemental analysis and spectral data (1H NMR, IR and MS).
Discovery of tetrahydrotetramethylnaphthalene analogs as adult T-cell leukemia cell-selective proliferation inhibitors in a small chemical library constructed based on multi-template hypothesis
Nakamura, Masahiko,Hamasaki, Takayuki,Tokitou, Maiko,Baba, Masanori,Hashimoto, Yuichi,Aoyama, Hiroshi
experimental part, p. 4740 - 4746 (2009/10/10)
Adult T cell leukemia (ATL), caused by infection of human T-lymphotropic virus type 1 (HTLV-1), has a poor prognosis and curative therapy is unavailable, so it is important to find or design superior lead compounds for the drug treatment of ATL. We used our micro-reversed fragment-based drug design hypothesis and multi-template hypothesis to extract the tetrahydrotetramethylnaphthalene (TMN) skeleton from tamibarotene, a useful medicament for the treatment of acute promyelocytic leukemia (APL). Structural development of TMN yielded highly ATL cell-selective growth inhibitors, including 2-acetyl-3-hydroxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene (6). Structure-activity relationship analysis suggests the existence of a specific target molecule for ATL cell-selective inhibition of proliferation through G2 arrest.
