CAS: 86-42-0; 4-((7-Chloroquinolin-4-yl)Amino)-2-((Diethylamino)Methyl)Phenol

该化合物是一种4-氨基甲酸药物,与氯quine密切相关,主要用于治疗和预防疟疾,特别是在抗抗其他抗疟药物普遍的地区.阿莫迪亚奎因的化学配方是C18H20ClN3O,其特点是氯组,一个管状环和一个氨基亚基安组,有助于其药理活动.阿莫迪亚奎因表现出类似于氯quine的一种行动机制,它干扰疟疾寄生虫的肝氧化过程,最终导致其死亡.该物质通常以盐盐盐的形式施用,这提高了其溶性.虽然它有效,但阿莫迪亚奎可产生副作用,包括胃肠紊乱和潜在的血病症,如腺细胞病.由于它的安全性特征和抗药性,近年来其使用已变得更加有限,因为保健提供者往往选择替代治疗.

结构式图片

物理性质

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上下游产品

CAS号86-98-6 4,7-二氯喹啉 | CAS号123-30-8 对氨基苯酚 | CAS号109-89-7 二乙胺 | CAS号121-78-8 4-乙酰胺-2-二乙氨甲基苯酚 | CAS号103-90-2 对乙酰氨基苯酚 | CAS号100-02-7 对硝基苯酚 | CAS号51387-92-9 4-氨基-Alpha-二乙胺基... | CAS号79352-78-6 去乙基阿莫地喹

合成工艺路线路线简述

  • 合成目标产物 Amodiaquine 主要起始原料 4,7-Dichloroquinoline And 4-Aminophenol And Diethylamine
  • 121-78-8 = 86-42-0
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Water; 120 °C2.1 Reagents: Oxygen Catalysts: Cupric Acetate,Palladium Diacetate,4,4′-Dimethoxy-2,2′-Bipyridine Solvents: Pivalic Acid; 4 - 12 H,140 °C; 140 °C -> Rt2.2 Reagents: Sodium Carbonate Solvents: Water; Rt
    标题:Aerobic Dehydrogenative Aromatization In The Preparation Of 4-Aminoquinoline Derivatives By Synergistic Pd/cu Catalysis
    作者:Chen,Fei; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2023 卷标:88(22) 页码:15589-15596]

    121-78-8 = 86-42-0
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Ethanol; 2 H,100 - 110 °C1.2 Reagents: Sodium Carbonate Solvents: Water; Neutralized2.1 Solvents: Ethanol; 24 H,80 °C
    标题:The Synthesis Of Amodiaquine Hydrochloride
    作者:Nguyen,Van Hung; Et Al
    参考文献:Tap Chi Hoa Hoc 日期:2012 卷标:50(2) 页码:174-177]

    103-90-2 = 86-42-0
    反应条件:1.1 Solvents: Ethanol; 100 °C1.2 Ph 9 - 102.1 Reagents: Hydrochloric Acid Solvents: Water; 120 °C3.1 Reagents: Oxygen Catalysts: Cupric Acetate,Palladium Diacetate,4,4′-Dimethoxy-2,2′-Bipyridine Solvents: Pivalic Acid; 4 - 12 H,140 °C; 140 °C -> Rt3.2 Reagents: Sodium Carbonate Solvents: Water; Rt
    标题:Aerobic Dehydrogenative Aromatization In The Preparation Of 4-Aminoquinoline Derivatives By Synergistic Pd/cu Catalysis
    作者:Chen,Fei; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2023 卷标:88(22) 页码:15589-15596]

    = 86-42-0
    反应条件:1.1 Solvents: Toluene; 140 °C2.1 6 - 8 H,120 °C; 120 °C -> Rt2.2 Reagents: Water; 0 °C; Overnight,Rt2.3 Reagents: Sodium Carbonate Solvents: Water; Ph 8 - 10,Rt3.1 Reagents: Oxygen Catalysts: Cupric Acetate,Palladium Diacetate,4,4′-Dimethoxy-2,2′-Bipyridine Solvents: Pivalic Acid; 4 - 12 H,140 °C; 140 °C -> Rt3.2 Reagents: Sodium Carbonate Solvents: Water; Rt
    标题:Aerobic Dehydrogenative Aromatization In The Preparation Of 4-Aminoquinoline Derivatives By Synergistic Pd/cu Catalysis
    作者:Chen,Fei; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2023 卷标:88(22) 页码:15589-15596]

    = 86-42-0
    反应条件:1.1 Solvents: Dichloromethane; 1 H,Rt; Rt -> 60 °C2.1 Solvents: Ethanol; 100 °C2.2 Ph 9 - 103.1 Reagents: Hydrochloric Acid Solvents: Water; 120 °C4.1 Reagents: Oxygen Catalysts: Cupric Acetate,Palladium Diacetate,4,4′-Dimethoxy-2,2′-Bipyridine Solvents: Pivalic Acid; 4 - 12 H,140 °C; 140 °C -> Rt4.2 Reagents: Sodium Carbonate Solvents: Water; Rt
    标题:Aerobic Dehydrogenative Aromatization In The Preparation Of 4-Aminoquinoline Derivatives By Synergistic Pd/cu Catalysis
    作者:Chen,Fei; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2023 卷标:88(22) 页码:15589-15596]

    2623-33-8 = 86-42-0
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Water; Rt; 1 H,80 - 90 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; Acidified2.1 Solvents: Ethanol; 4.5 H,80 - 90 °C2.2 Reagents: Sodium Carbonate Solvents: Water; Neutralized3.1 Reagents: Hydrochloric Acid Solvents: Ethanol; 2 H,100 - 110 °C3.2 Reagents: Sodium Carbonate Solvents: Water; Neutralized4.1 Solvents: Ethanol; 24 H,80 °C
    标题:The Synthesis Of Amodiaquine Hydrochloride
    作者:Nguyen,Van Hung; Et Al
    参考文献:Tap Chi Hoa Hoc 日期:2012 卷标:50(2) 页码:174-177]

    51387-92-9 + 86-98-6 = 86-42-0
    反应条件:1.1 Solvents: Ethanol; 24 H,80 °C
    标题:The Synthesis Of Amodiaquine Hydrochloride
    作者:Nguyen,Van Hung; Et Al
    参考文献:Tap Chi Hoa Hoc 日期:2012 卷标:50(2) 页码:174-177]

    51387-92-9 + 21617-15-2 = 86-42-0
    反应条件:1.1 Reagents: Oxygen Catalysts: Cupric Acetate,Palladium Diacetate,4,4′-Dimethoxy-2,2′-Bipyridine Solvents: Pivalic Acid; 4 - 12 H,140 °C; 140 °C -> Rt1.2 Reagents: Sodium Carbonate Solvents: Water; Rt
    标题:Aerobic Dehydrogenative Aromatization In The Preparation Of 4-Aminoquinoline Derivatives By Synergistic Pd/cu Catalysis
    作者:Chen,Fei; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2023 卷标:88(22) 页码:15589-15596]

    21617-14-1 = 86-42-0
    反应条件:1.1 6 - 8 H,120 °C; 120 °C -> Rt1.2 Reagents: Water; 0 °C; Overnight,Rt1.3 Reagents: Sodium Carbonate Solvents: Water; Ph 8 - 10,Rt2.1 Reagents: Oxygen Catalysts: Cupric Acetate,Palladium Diacetate,4,4′-Dimethoxy-2,2′-Bipyridine Solvents: Pivalic Acid; 4 - 12 H,140 °C; 140 °C -> Rt2.2 Reagents: Sodium Carbonate Solvents: Water; Rt
    标题:Aerobic Dehydrogenative Aromatization In The Preparation Of 4-Aminoquinoline Derivatives By Synergistic Pd/cu Catalysis
    作者:Chen,Fei; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2023 卷标:88(22) 页码:15589-15596]

    103-90-2 = 86-42-0
    反应条件:1.1 Solvents: Ethanol; 4.5 H,80 - 90 °C1.2 Reagents: Sodium Carbonate Solvents: Water; Neutralized2.1 Reagents: Hydrochloric Acid Solvents: Ethanol; 2 H,100 - 110 °C2.2 Reagents: Sodium Carbonate Solvents: Water; Neutralized3.1 Solvents: Ethanol; 24 H,80 °C
    标题:The Synthesis Of Amodiaquine Hydrochloride
    作者:Nguyen,Van Hung; Et Al
    参考文献:Tap Chi Hoa Hoc 日期:2012 卷标:50(2) 页码:174-177]

    = 86-42-0
    反应条件:1.1 6 H,60 - 70 °C1.2 Reagents: Sodium Hydroxide2.1 Reagents: Sodium Hydroxide Solvents: Water; Rt; 1 H,80 - 90 °C2.2 Reagents: Hydrochloric Acid Solvents: Water; Acidified3.1 Solvents: Ethanol; 4.5 H,80 - 90 °C3.2 Reagents: Sodium Carbonate Solvents: Water; Neutralized4.1 Reagents: Hydrochloric Acid Solvents: Ethanol; 2 H,100 - 110 °C4.2 Reagents: Sodium Carbonate Solvents: Water; Neutralized5.1 Solvents: Ethanol; 24 H,80 °C
    标题:The Synthesis Of Amodiaquine Hydrochloride
    作者:Nguyen,Van Hung; Et Al
    参考文献:Tap Chi Hoa Hoc 日期:2012 卷标:50(2) 页码:174-177
4-乙酰胺-2-二乙氨甲基苯酚置于盐酸体系中,化学反应生成 阿莫地喹
参考文献:氟取代对阿莫地喹的代谢和抗疟活性的影响.
标题:氟取代对阿莫地喹的代谢和抗疟活性的影响.
摘要:阿莫地喹(aq)(2)是一种4-氨基喹啉抗疟药,可引起不良副作用,例如粒细胞缺乏症和肝损害.据信,观测到的药物毒性与亲电子代谢物氨二喹醌亚胺(aqqi)的形成有关,后者可以与细胞大分子结合并引发超敏反应.5'-氟氨二喹(5'-Faq,3),5',6'-二氟氨二喹(5',6'-Difaq,4),2',6'-二氟氨二喹(2',6'-Difaq,5),2',5',6'-三氟嘧啶(2',5',6'-Trifaq,6)和4'-Dehydroxy-4'-氟嘧啶(4'-Deoh-4'-Faq,7)合成以评估氟取代对阿莫地喹的氧化潜能,代谢和体外抗疟活性的影响.通过循环伏安法测量氧化电位,观测到在2',6'-和4'-位置的取代(2',6'-Difaq和4'-Deoh-4'-Faq)产生了类似物具有比母体药物明显更高的氧化电位.在2',6'-位和4'-位的氟取代也产生了对生物活化更具抗性的类似物.因此2'
DOI:10.1021/jm00035A017

海关参考信息

专利信息


专利号:WO-2013138200-A1
优先权日:2012-03-13
标 题 :Green chemistry synthesis of the malaria drug amodiaquine and analogs thereof
发明人：FORTUNAK JOSEPH MARIAN; KULKARNI AMOL ANANT; KING CHRISTOPHER
权利人:UNIV HOWARD
摘要:Methods are provided for a green chemistry one-pot synthesis of amodiaquine and amodiaquine analogs. The methods have a lower environmental impact, lower investment cost, reduced amounts of byproducts and impurities, and a shorter synthesis time, compared to current conventional synthesis methods. The methods reduce the total number of steps in the synthesis from four to five down to two, thereby simplifying production; and allow a reduced number of solvents and reagents to be used in production, thereby reducing the waste generated in the synthesis. The methods can reduce the waste to about 3-5 kilograms of waste generated per kilogram of product produced; and surprisingly improve the overall yield from 60-65% to greater than 90% as compared to the current conventional synthesis methods for amodiaquine and its analogs.

专利号:US-2012100555-A1
优先权日:2009-06-29
标题 :Synthesis And Use Of Fluorophore-Tagged Antimalarials
发明人：LEAR MARTIN JAMES; TAN KEVIN SHYONG WEI
权利人:LEAR MARTIN JAMES; TAN KEVIN SHYONG WEI
摘要:This invention includes a fluorophore-tagged antimalarial represented by the following structural formula (1) or a salt thereof. This invention relates to the synthesis of fluorophore-tagged antimalarials and describes the synthesis of a fluorophore-tagged antimalarial. These fluorophore-tagged antimalarials can be used to image live cells to determine the location of the antimalarial in the cell, identify drug resistance and growth related pathways in Plasmodium isolates, identify new drug targets and chemo-sensitizers to reverse drug resistance.

专利号:US-9409879-B2
优先权日:2011-03-29
标 题 :Total synthesis of redox-active 1.4-naphthoquinones and their metabolites and their therapeutic use as antimalarial and schistomicidal agents
发明人：DAVIOUD-CHARVET ELISABETH; LANFRANCHI DON ANTOINE; JOHANN LAURE; WILLIAMS DAVID LEE; CESAR RODO ELENA
权利人:DAVIOUD-CHARVET ELISABETH; LANFRANCHI DON ANTOINE; JOHANN LAURE; WILLIAMS DAVID LEE; CESAR RODO ELENA; CENTRE NAT RECH SCIENT
摘要:Naphthoquinones, azanaphthoquinones and benxanthones, their process of synthesis and methods of their use as antimalarial or antischistosomal agents.

专利号:US-7427483-B2
优先权日:2006-02-24
标题:Utilization of nucleotide probes in ELISA procedure for the quantitative determination of Plasmodium falciparum DNA in malaria
发明人：NGUYEN KHUE VU
权利人:VISTA BIOLOG CORP
摘要:The present invention is the development of a simple and specific quantitative method for the determination of P. falciparum DNA in malaria that involves the direct detection of the highly 42-kDa conserved C-terminal region of P. falciparum merozoite surface protein (MSP1) gene. This procedure entails the amplification of the 42-kDa C-terminal region of the MSP1 gene by using the PCR technique in the presence of digoxigenin-11-dUTP and the synthesis of the specific biotin labeled nucleotide probes directed to the 42-kDa C-terminal region of the MSP1 gene. These specific probes are then used in the Enzyme Linked Immunosorbent Assay (ELISA) for the quantitative determination of the 42-kDa C-terminal region of the MSP1 gene which leads to the quantitative determination of P. falciparum DNA in malaria for quantitative diagnostic purpose as well as for monitoring the efficacy of antimalarial treatment.

专利号:WO-2023187827-A1
优先权日:2022-03-30
标题:A pharmaceutical composition comprising an inhibitor of glutamine synthetase enzyme to combat artemisinin resistance in malaria
发明人：ARUN NAGARAJ VISWANATHAN; PADMANABAN GOVINDARAJAN; GHOSH SOURAV; KUNDU RAJIB; CHANDANA MANJUNATHA; ANAND ADITYA
权利人:INST OF LIFE SCIENCES
摘要:The present disclosure relates to a pharmaceutical composition to combat artemisinin resistance in malaria with the identification of Plasmodium falciparum (Pf) glutamine synthetase (GS) as a drug target. Pf Gs is important for maintaining asparagine levels in the parasite and promote protein synthesis. Since ART-resistant parasites undergo fitness loss in amino acid/nutrient- limiting conditions and GS levels are upregulated during ART exposure, targeting Pf GS and asparagine requirement can be harnessed to prevent ART resistance. The present disclosure also provides a method of suppressing the growth of Plasmodium falciparum and a method of treating malaria using GS inhibitors.

专利号:US-10550127-B1
优先权日:2017-02-08
标题:Indanylaminoazadihydrobenzofuranylacetic acids, pharmaceutical compositions for the treatment of diabetes
发明人：ECKHARDT MATTHIAS; WAGNER HOLGER; PETERS STEFAN
权利人:BOEHRINGER INGELHEIM INT
摘要:The present invention relates to compounds of general formula I, n nwherein the groups R, R 1 , R 2 , m and n are defined herein, which have valuable pharmacological properties, in particular bind to the GPR40 receptor and modulate its activity. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2. Furthermore, the invention relates to novel intermediates, useful for the synthesis of compounds of formula I.

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主要参考文献


1: Gil JP. Amodiaquine pharmacogenetics. Pharmacogenomics. 2008 Oct;9(10):1385-90. doi: 10.2217/14622416.9.10.1385. (2):CD000016. doi: 10.1002/14651858.CD000016. Update in: Cochrane Database Syst Rev. 2003;(2):CD000016. (2):CD000016. doi: 10.1002/14651858.CD000016. 348(9042):1659-60. doi: 10.1016/S0140-6736(05)65723-6. 16(7):1079-85. doi: 10.1517/13543784.16.7.1079. 1(9):298-9. doi: 10.5694/j.1326-5377.1977.tb130706.x. 348(9036):1196-201. doi: 10.1016/S0140-6736(96)06217-4. 4(12):721-2; discussion 722. doi: 10.1016/S1473-3099(04)01198-3. (4):CD000386. doi: 10.1002/14651858.CD000386. Update in: Cochrane Database Syst Rev. 2005;(4):CD000386. (2):CD000386. doi: 10.1002/14651858.CD000386. Update in: Cochrane Database Syst Rev. 2001;(4):CD000386. 6(6):631-5. doi: 10.1517/14740338.6.6.631. 2(6029):214-5. doi: 10.1136/bmj.2.6029.214.
13: Sakurai Y, Sakakibara N, Toyama M, Baba M, Davey RA. Novel amodiaquine derivatives potently inhibit Ebola virus infection. Antiviral Res. 2018 Dec;160:175-182. doi: 10.1016/j.antiviral.2018.10.025. Epub 2018 Nov 3.
14: Willems S, Müller M, Ohrndorf J, Heering J, Proschak E, Merk D. Scaffold Hopping from Amodiaquine to Novel Nurr1 Agonist Chemotypes via Microscale Analogue Libraries. ChemMedChem. 2022 Apr 20;17(8):e202200026. doi: 10.1002/cmdc.202200026. Epub 2022 Feb 21.

合成参考文献


参考文献:10.1186/1475-2875-9-53
摘要:Sowunmi A, Adewoye EO, Gbotsho GO, Happi CT, Sijuade A, Folarin OA, Okuboyejo TM, Michael OS. Factors contributing to delay in parasite clearance in uncomplicated falciparum malaria in children. Malaria Journal. 2010 Feb 15;9(1):53. doi: 10.1186/1475-2875-9-53.
参考文献:10.1186/1475-2875-10-187
摘要:Kwansa-Bentum B, Ayi I, Suzuki T, Otchere J, Kumagai T, Anyan WK, Osei JH, Asahi H, Ofori MF, Akao N, Wilson MD, Boakye DA, Ohta N. Plasmodium falciparum isolates from southern Ghana exhibit polymorphisms in the SERCA-type PfATPase6 though sensitive to artesunate in vitro. Malaria Journal. 2011 Jul 11;10(1):187. doi: 10.1186/1475-2875-10-187.
参考文献:10.1186/1475-2875-4-56
摘要:Helleberg M, Goka BQ, Akanmori BD, Obeng-Adjei G, Rodriques O, Kurtzhals JA. Bone marrow suppression and severe anaemia associated with persistent Plasmodium falciparum infection in African children with microscopically undetectable parasitaemia. Malaria Journal. 2005 Dec 01;4(1):56. doi: 10.1186/1475-2875-4-56.
参考文献:10.1186/1471-2458-11-573
摘要:Dicko A, Toure SO, Traore M, Sagara I, Toure OB, Sissoko MS, Diallo AT, Rogier C, Salomon R, de Sousa A, Doumbo OK. Increase in EPI vaccines coverage after implementation of intermittent preventive treatment of malaria in infant with Sulfadoxine -pyrimethamine in the district of Kolokani, Mali: results from a cluster randomized control trial. BMC Public Health. 2011 Jul 18;11():573.
参考文献:10.1371/journal.pone.0021237
摘要:Penna-Coutinho J, Cortopassi WA, Oliveira AA, França TCC, Krettli AU. Antimalarial Activity of Potential Inhibitors of Plasmodium falciparum Lactate Dehydrogenase Enzyme Selected by Docking Studies. PLoS ONE. 2011 Jul 14;6(7):e21237. doi: 10.1371/journal.pone.0021237.
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