CAS: 17422-74-1; 4-Oxo-4H-Chromene-3-Carbaldehyde

该化合物是一种属于铬类的有机化合物,其特点是苯丙酮结构,该化合物在铬环的3个位置上有一个气态组(-CHO),有助于其活性及有机合成的潜在应用;该化合物一般是黄色至褐色固体,在乙醇和丙酮等有机溶剂中可溶解,但在水中可溶性较小; 3-福色酮展示了显著的生物活动,包括抗微生物和抗癌特性,使其对药用化学感兴趣;该化合物的结构允许进行各种化学改造,可以加强其生物活动或改变其物理特性;该化合物可参与各种化学反应,包括凝聚和循环,使其成为合成有机化学的多用途建筑块.此外,其衍生物可能表现出氟化作用,可用于分析应用.

结构式图片

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

o-hydroxyacetophenone N,N-dimethyl-formamide 2-(4-oxo-4H-1-benzopyran-3-yl)-1,3-dioxolane 3-[bis(acetyloxy)methyl]-4H-1-benzopyran-4-one-2-phenyloxazol-5-one4,5-Dihydro-4-(4-oxo-4H-1-benzopyran-3-yl)methylene-2-phenyloxazol-5-one 3(4',5'-diphenylimidazole-2'-yl)-4(H)-oxo-1-benzopyran H-benzo[b]chromeno[2,3-e][1,4]diazepin-13-one6-methyl-6H-benzo[b]chromeno[2,3-e][1,4]diazepin-13-one H-benzo[b]chromeno[2,3-e][1,4]diazepin-13-one6-phenyl-6H-benzo[b]chromeno[2,3-e][1,4]diazepin-13-one

合成工艺路线路线简述

    乙酸苯酯置于aluminum (III) Chloride,草酰氯体系中,化学反应生成色酮-3-甲醛
    参考文献:新型取代的4 H-Chromen-1,2,3,4-四氢嘧啶-5-羧酸酯的合成,构效关系作为潜在的抗分枝杆菌和抗癌药
    标题:新型取代的4 H-Chromen-1,2,3,4-四氢嘧啶-5-羧酸酯的合成,构效关系作为潜在的抗分枝杆菌和抗癌药
    摘要:合成了一系列4 H-1,2,3,4-四氢嘧啶-5-羧甲基铬衍生物7A-7Zb,8A-8D和9A-9D并筛选了其对结核分枝杆菌h 37 Rv的体外抗分枝杆菌活性.(mtb)和针对三种人类癌细胞系(包括a549,Sk-N-Sh和hela)的细胞毒性.结果表明,六种化合物的效价更高,而7Za与标准药物乙胺丁醇和环丙沙星相比,它是最有效的抗分枝杆菌衍生物.但是,有12种化合物对人神经母细胞瘤细胞系表现出细胞毒性.其中,与标准药物阿霉素相比,化合物7V最有效.这是首次针对这种新型的4 H-Chromen-1,2,3,4-Tetrahydropyrimidine-5-Carboxylates分配体外抗分枝杆菌,抗癌和结构-活性关系的报告.
    Doi:10.1016/j.Bmcl.2011.03.079

    海关参考信息

    专利信息


    专利号:US-7056348-B2
    优先权日:2001-04-19
    标题:5-aryl-1,3,3-trimethyl-2-methylene-indoline derivatives and salts thereof, methods for the production and use of said compounds for the temporary coloration of fibers
    发明人:SAUTER GUIDO; BRAUN HANS-JUERGEN; REICHLIN NADIA
    权利人:WELLA AG
    摘要:A method for the synthesis of 5-aryl-1,3,3,-trimethyl-2-methylene-indoline derivatives of Formula (I) or its salts of Formula (Ia) wherein 1 mole of a 5-aryl-2,3,3-trimethyl-3H-indole derivative of Formula (VII) is reacted for 1 to 44 hours at a temperature of 20° to 180° C. in an apolar, aprotic or polar, protic or polar aprotic solvent with 1 to 50 moles of a compound of Formula R1-A; new compounds of Formulas (I)/(Ia) and (V), obtainable by this method as well as an agent containing at least one compound of Formula (I)/(Ia) and a carbonyl/imine compound for dyeing keratinic fibers and a method for temporarily dyeing keratin fibers, for which the keratin fiber is dyed with the aforementioned agent and the dyeing, so obtained, is removed again at any later time by a sulfite preparation.

    专利号:WO-0053313-A2
    优先权日:1999-03-09
    标 题:Lanthanide catalysts for synthesis of compounds and combinatorial libraries

    专利号:US-3984441-A
    优先权日:1971-06-21
    标 题:Chromonealdehyde compounds and process for the production thereof
    发明人:NOHARA AKIRA; UMETANI TOMONOBU; MIYATA YOSHIBUMI; SANNO YASUSHI
    权利人:TAKEDA CHEMICAL INDUSTRIES LTD
    摘要:There are provided compounds of the general formula ##SPC1## n Wherein R is a hydroxy, alkyl, acyloxy, halogen, nitro, substituted or unsubstituted amino, alkoxy, carboxy or a group derived from a carboxy group and m is 0, 1 or 2 except where m is 2, the two R groups are both hydroxy groups. n The present invention is also concerned with a process for preparing the chromonealdehyde compounds. The chromonealdehyde compounds are characterized by antiallergic properties and are therefore useful as prophylactic and therapeutic agents for allergic asthma, allergic dermatitis and other allergic diseases and also are valuable as intermediates for the synthesis of other pharmaceutical compounds having the chromone nucleus.

    专利号:US-2013164265-A1
    优先权日:2011-12-21
    标题 :Skin care compositions
    发明人:FLAVIN DANA; OBENLAND SIGRID
    权利人:FLAVIN DANA; OBENLAND SIGRID
    摘要:This invention provides compositions and methods of manufacturing such compositions that employ GRAS compounds which can act to promote the generation of stem, epidermal or other skin cells in the epidermis, activation of collagen synthesis, activation of hyaluronic acid synthesis, enhanced skin hydration, and dermal healing by stimulating stem cell and fibroblast migration to sites of needed repair. These compositions and methods are useful for rejuvenating the skin and for treating some skin-related aging or other dermal damaging conditions, including wrinkle reduction and treatment of minor dermal wounds.

    专利号:US-2014328952-A1
    优先权日:2011-12-21
    标题:Topical compositions
    发明人:FLAVIN DANA
    权利人:FLAVIN DANA
    摘要:This invention provides compositions and methods of manufacturing such compositions that employ GRAS compounds which can act to promote the generation of stem, epidermal or other skin cells in the epidermis, activation of collagen synthesis, activation of hyaluronic acid synthesis, enhanced skin hydration, and dermal healing by stimulating stem cell and fibroblast migration to sites of needed repair. These compositions and methods are useful for rejuvenating the skin and for treating some skin-related aging or other dermal damaging conditions, including wrinkle reduction and treatment of minor dermal wounds.

    专利号:US-2012316192-A1
    优先权日:2011-06-09
    标题:Substituted indolo [2,3-a] quinolizines
    发明人:WALDMANN HERBERT; KUMAR KAMAL; HUEBEL KATJA; PRIES VERENA; DUECKERT HEIKO; MENNINGER SASCHA; ZIEGLER SLAVA; BRUSS HANNA; KHEDKAR VIVEK; ESCHENBRENNER VINCENT
    权利人:WALDMANN HERBERT; KUMAR KAMAL; HUEBEL KATJA; PRIES VERENA; DUECKERT HEIKO; MENNINGER SASCHA; ZIEGLER SLAVA; BRUSS HANNA; KHEDKAR VIVEK; ESCHENBRENNER VINCENT
    摘要:The present invention relates to novel substituted indolo[2,3-a]quinolizines and stereoisomeric forms thereof and/or pharmaceutically acceptable salts of these compounds as well as pharmaceutical compositions containing at least one of these substituted indolo[2,3-a]quinolizines together with pharmaceutically acceptable carrier, excipient and/or diluents. Said novel substituted indolo[2,3-a]quinolizines have been identified as useful for the prophylaxis and treatment of cancer by the induction of strong mitotic delays, chromosomal misalignments and mitotic tri- and multipolarization leading to cell cycle stop and apoptosis. Furthermore a synthesis for preparation of the substituted indolo[2,3-a]quinolizines is disclosed in the present invention.
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    主要参考文献

    [参考文献]: Andrey S Plaskon, Et Al. Synthesis Of Quinolines From 3-Formylchromone. J Org Chem. 2008 Aug 1;73(15):6010-3.
    [参考文献]: Khalid M Khan, Et Al. 3-Formylchromones: Potential Antiinflammatory Agents. Eur J Med Chem. 2010 Sep;45(9):4058-64.
    [参考文献]: M Ilamathi, Et Al. Formylchromone Exhibits Salubrious Effects Against Nitrosodiethylamine Mediated Early Hepatocellular Carcinogenesis In Rats. Chem Biol Interact. 2014 Aug 5:219:175-83.
    [参考文献]: Pedatsur Neta, Et Al. Loss Of H2 And Co From Protonated Aldehydes In Electrospray Ionization Mass Spectrometry. Rapid Commun Mass Spectrom. 2014 Sep 15;28(17):1871-82.
    [参考文献]: Zeba N Siddiqui, Et Al. Thermal Solvent-Free Synthesis Of Chromonyl Chalcones, Pyrazolines And Their In Vitro Antibacterial, Antifungal Activities. J Enzyme Inhib Med Chem. 2012 Feb;27(1):84-91.

    合成参考文献


    摘要:Lubell, W. D.; St-Cyr, D. J.; Dufour-Gallant, J.; Hopewell, R.; Boutard, N.; Kassem, T.; Dörr, A.; Zelli, R., Science of Synthesis Knowledge Updates, (2013) 1, 225.
    摘要:Gao, W.-C.; Tian, J., Science of Synthesis Knowledge Updates, (2020) 3, 301.
    摘要:Spitzner, D., Science of Synthesis Knowledge Updates, (2016) 1, 20.
    摘要:von Angerer, S., Science of Synthesis Knowledge Updates, (2011) 1, 277.
    摘要:Leung, M.-k.; Chou, C.-M.; Luh, T.-Y., Science of Synthesis Knowledge Updates, (2018) 2, 405.
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