CAS: 95-24-9; 6-Chlorobenzothiazol-2-Ylamine

该化合物是一种环环有机化合物,其核心为苯并氮-甲醇,在6点被氯组替代,在2点被矿组替代,该结构赋予了适合用作药物和农用化学合成的多功能中间体的回活动性,其富电子芳香系统和功能组可进行选择性修改,使其对构建复杂分子具有价值. 氯代成分增加了电益替代潜力,而该矿组则允许通过凝结或混合反应进一步衍生出该化合物,该化合物在药用化学中特别有助于开发生物活性手持式手架. 高纯度能确保研究和工业应用的一贯性能.

结构式图片

物理性质

MSDS等安全信息

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

CAS号333-20-0 硫氰酸钾 | CAS号106-47-8 对氯苯胺 | CAS号3696-23-9 4-氯苯基硫脲 | CAS号540-72-7 硫氰酸钠 | CAS号14779-13-6 μ-disulfido-1,2... | CAS号20265-96-7 对氯苯胺盐酸盐 | CAS号110766-84-2 8-chloro-3,5-di... | CAS号3622-23-9 2,6-二氯苯并噻唑 | CAS号38338-20-4 2-氨基-4-溴-6-氯苯并噻唑 | CAS号3507-17-3 2-溴-6-氯苯并噻唑 | CAS号51011-54-2 1-(6-氯-1,3-苯并噻唑... | CAS号34551-19-4 6-氯-N-甲基-2-苯并噻唑胺 | CAS号58199-49-8 6-氯-3-甲基-3H-苯并噻... | CAS号30459-51-9 2(3H)-Benzothia... | CAS号23474-98-8 2-氨基-5-氯苯硫酚 | CAS号31183-89-8 2,2'-Disulfaned...

合成工艺路线路线简述

  • 1762-95-4 = 95-24-9
    反应条件:1.1 Reagents: Acetic Acid,Cupric Chloride; 1.5 H,Rt; Cooled1.2 Reagents: Hydrochloric Acid Solvents: Water; 30 Min,Heated; Cooled1.3 Reagents: Sodium Carbonate Solvents: Water; Neutralized
    标题:Studies Of Solute-Solvent Interactions And Applications Of Green And Blue Complexes Of Copper(Ii) Palmitate With 2-Amino Benzothiazoles
    作者:Mathur,Neha
    参考文献:Journal Of Current Chemical & Pharmaceutical Sciences 日期:2011 卷标:1(1) 页码:37-51]

    333-20-0 = 95-24-9
    反应条件:1.1 Catalysts: Silica,Boron Trifluoride (Reaction Product With Silica Gel) Solvents: Acetonitrile; 30 Min,0 °C1.2 Reagents: Bromine Solvents: Acetonitrile; 60 Min,< 0 °C; 6.5 H,Rt1.3 Reagents: Sodium Hydroxide Solvents: Water; Neutralized
    标题:Efficient And Facile Protocol For One-Pot Synthesis Of 2-Amino-Substituted Benzothiazoles Catalyzed By Nano-Bf3/sio2 Under Mild Conditions
    作者:Naeimi,Hossein; Heidarnezhad,Arash
    参考文献:Research On Chemical Intermediates 日期:2016 卷标:42(12) 页码:7855-7868]

    333-20-0 = 95-24-9
    反应条件:1.1 Reagents: Oxygen Catalysts: Boron Trifluoride Etherate,N,N,N′,N′-Tetramethylethylenediamine,Copper(Ii) Triflate Solvents: Dimethyl Sulfoxide; 12 H,100 °C
    标题:Copper-Catalyzed Aerobic Oxidative Regioselective Thiocyanation Of Aromatics And Heteroaromatics
    作者:Jiang,Huanfeng; Yu,Wentao; Tang,Xiaodong; Li,Jianxiao; Wu,Wanqing
    参考文献:Journal Of Organic Chemistry 日期:2017 卷标:82(18) 页码:9312-9320]

    333-20-0 = 95-24-9
    反应条件:1.1 Reagents: Bromine Solvents: Acetic Acid; 42 Min,25 °C; 2 H,25 °C1.2 Reagents: Ammonia Solvents: Water; Ph 7
    标题:Application Of Quality By Design In The Synthesis Of 6-Substituted-2-Aminobenzothiazole
    作者:Bonde,Chandrakant; Vedala,Deepti; Bonde,Smita
    参考文献:Journal Of Pharmacy Research (Mohali 日期:2015 卷标:9(9) 页码:573-580]

    333-20-0 = 95-24-9
    反应条件:1.1 Solvents: Acetic Acid; 2 H,15 - 20 °C1.2 Reagents: Bromine Solvents: Acetic Acid; 1 H,< 20 °C; 2 - 4 H,Rt1.3 Reagents: Ammonia Solvents: Water; Neutralized,Rt
    标题:Aromatic Amine Containing Amino Side Chain As Acetylcholinesterase Inhibitor And Its Preparation
    参考文献:China]

    1762-95-4 = 95-24-9
    反应条件:1.1 Reagents: Acetic Acid,Bromine Solvents: Water; 6.5 Min,40 °C
    标题:Docking,Synthesis,Characterization And Evaluation Of Novel Cdk2 Inhibitors: Benzothiazole Derivatives
    作者:Priyadharsini,R.; Jerad Suresh,A.; Sathish,M.; Kavitha,S.; Selvin Thanuja,C.
    参考文献:International Journal Of Pharmacy And Pharmaceutical Sciences 日期:2012 卷标:4 页码:574-584]

    2942-10-1 + 3425-46-5 = 95-24-9
    反应条件:1.1 Reagents: Trifluoromethanesulfonic Anhydride,Iodobenzene Diacetate Catalysts: Iodine Solvents: Water; 6 H,110 °C
    标题:Iodine-Catalyzed Amination Of Benzothiazoles With Ksecn In Water To Access Primary 2-Aminobenzothiazoles
    作者:Zhu,Yu-Shen; Shi,Linlin; Fu,Lianrong; Chen,Xiran; Zhu,Xinju; Et Al
    参考文献:Chinese Chemical Letters 日期:2022 卷标:33(3) 页码:1497-1500]

    = 95-24-9
    反应条件:1.1 Solvents: Ethanol; Reflux
    标题:Exploration Of Novel Ureidobenzothiazole Library Against Neuroinflammation
    作者:Han,Minsoo; Park,Chan-Ho; Nam,Kee Dal; Cho,Sung-Woo; Hahn,Hoh-Gyu
    参考文献:Bulletin Of The Korean Chemical Society 日期:2011 卷标:32(10) 页码:3805-3808]

    333-20-0 = 95-24-9
    反应条件:1.1 Reagents: Iodate(1-),Dichloro-,Sodium Solvents: Dimethyl Sulfoxide,Water; 5 Min,Rt; Rt -> 70 °C; 2 H,70 °C1.2 Reagents: Water
    标题:A Novel System For The Synthesis Of 2-Aminobenzothiazoles Using Sodium Dichloroiodate
    作者:Telvekar,Vikas N.; Bachhav,Harshal M.; Bairwa,Vinod Kumar
    参考文献:Synlett 日期:2012 卷标:23(15) 页码:2219-2222]

    = 95-24-9 [标题:Reaction Conditions
    标题:Synthesis Of 3-Substituted 7-(3,3-Dimethyl-1-Triazeno)-10-Methylphenothiazines As Potential Antitumor Agents
    作者:Lin,Ai Jeng; Kasina,Sudhaka
    参考文献:Journal Of Heterocyclic Chemistry 日期:1981 卷标:18(4) 页码:759-61]

    1762-95-4 = 95-24-9
    反应条件:1.1 Reagents: Bromine Solvents: Acetic Acid; < 10 °C; 30 Min,< 10 °C1.2 Reagents: Sodium Carbonate Solvents: Water; Basified
    标题:Synthesis And Pharmacological Evaluation Of 6-Substituted 2-Aminobenzothiazoles
    作者:Venkateshwarlu,L.; Sarangapani,M.; Eslawath,Upender Rao; Vadlakonda,Rajashekar
    参考文献:International Research Journal Of Pharmacy 日期:2018 卷标:9(9) 页码:110-116]

    1762-95-4 = 95-24-9
    反应条件:1.1 Reagents: Hydrochloric Acid,Bromine Solvents: Ethanol,Acetic Acid,Water; 2 H,Reflux
    标题:Synthesis And Docking Studies Of Pyrazole-Benzamide-Benzothiazole Conjugates As Xanthine Oxidase Inhibitor Candidates
    作者:Khadri M J,Nagesh; Ramu,Ramith; Al-Ghorbani,Mohammed; Khanum,Shaukath Ara
    参考文献:Journal Of Molecular Structure 日期:2023 卷标:1290]

    333-20-0 = 95-24-9
    反应条件:1.1 Solvents: 1-Butyl-3-Methylimidazolium Hydrogen Sulfate; Rt1.2 Reagents: Bromine Solvents: Chloroform; 0 - 5 °C; 4 H,Reflux
    标题:An Efficient Synthesis Of 2-Aminobenzothiazole And Its Derivatives In Ionic Liquids
    作者:Jangid,D. K.; Guleria,A.; Dhadda,S.; Yadav,K.; Goswami,P. G.; Et Al
    参考文献:International Journal Of Pharmaceutical Sciences And Research 日期:2017 卷标:8(7) 页码:2960-2964]

    1762-95-4 = 95-24-9
    反应条件:1.1 Solvents: Acetic Acid; Rt -> 10 °C1.2 Reagents: Bromine Solvents: Acetic Acid; < 10 °C; 12 H,10 °C1.3 Reagents: Ammonium Hydroxide Solvents: Water; Ph 9,Cooled
    标题:Benzo[4,5]Thiazolo[3,2-C][1,3,5,2]Oxadiazaborinines: Synthesis,Structural,And Photophysical Properties
    作者:Potopnyk,Mykhaylo A.; Volyniuk,Dmytro; Ceborska,Magdalena; Cmoch,Piotr; Hladka,Iryna; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2018 卷标:83(19) 页码:12129-12142]

    1762-95-4 = 95-24-9
    反应条件:1.1 Reagents: Acetic Acid Solvents: Water
    标题:Preparation Of 2-Aminobenzothiazoles By Electrogenerated Thiocyanogen
    作者:Kitahara,Kiyoshi; Takano,Yoshihito; Nishi,Hisao
    参考文献:Nippon Kagaku Kaishi 日期:1987 卷标:(7) 页码:1497-8]

    333-20-0 = 95-24-9
    反应条件:1.1 10 - 15 Min,Rt1.2 Reagents: Bromine Solvents: Acetic Acid; 2 - 3 H,10 - 15 °C; 10 - 15 Min,10 - 15 °C1.3 Reagents: Ammonia; Neutralized,5 - 10 °C
    标题:Synthesis And Biological Evaluation Of 1-(6-Chlorobenzo[d]Thiazol-2-Yl)-2-(Disubstituted Methylene)Hydrazine Derivatives
    作者:Sharma,Neetesh Kumar; Bhadauria,Raghvendra Singh
    参考文献:Journal Of Drug Delivery And Therapeutics 日期:2019 卷标:9 页码:561-572]

    333-20-0 = 95-24-9
    反应条件:1.1 Reagents: Bromine; < 10 °C; 3 H,< 10 °C
    标题:Novel Benzothiazole Hydrazine Carboxamide Hybrid Scaffolds As Potential In Vitro Gaba At Enzyme Inhibitors: Synthesis,Molecular Docking And Antiepileptic Evaluation
    作者:Jamal Gilani,Sadaf; Zaheen Hassan,Mohd.; Sarim Imam,Syed; Kala,Chandra; Prakash Dixit,Surya
    参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2019 卷标:29(14) 页码:1825-1830]

    333-20-0 = 95-24-9
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Ethanol,Water; Rt1.2 Reagents: Bromine Solvents: Acetic Acid; 1 H,Reflux; Cooled
    标题:Synthesis,Characterization And Anti-Inflammatory Activity Of Some 2-Aminobenzothiazole Derivatives
    作者:Venkatesh,P.; Pandeya,S. N.
    参考文献:International Journal Of Chemtech Research 日期:2009 卷标:1(4) 页码:1354-1358]

    3696-23-9 = 95-24-9
    反应条件:1.1 Reagents: Sodium Carbonate Solvents: Chlorobenzene; Rt -> 70 °C1.2 Reagents: Sulfuryl Chloride; 70 °C; 6 H,70 °C; 70 °C -> 20 °C1.3 Reagents: Sodium Hydroxide Solvents: Water
    标题:Study On Synthesis Of 2-Amino-6-Chlorobenzothiazole
    作者:Hang,Yan
    参考文献:Guangdong Huagong 日期:2011 卷标:38(9) 页码:54-55]

    333-20-0 = 95-24-9
    反应条件:1.1 Reagents: Bromine Solvents: Acetic Acid; < 5 °C; 3 H,0 - 10 °C1.2 Reagents: Ammonia Solvents: Water; Neutralized,Heated
    标题:Synthesis,Characterization And Biological Evaluation Of Some Heterocyclic Compounds Containing Ethoxyphthalimide Moiety Via Key Intermediate 6-Chloro 1,3 Benzothiazole 2-Amine
    作者:Sain,Devendra Kr.; Thadhancy,Bhawana; Joshi,Ajit; Hussain,Nasir; Talesara,Ganpat L.
    参考文献:Indian Journal Of Chemistry 日期:2010 卷标:(6) 页码:818-825
对氯苯胺置于ammonium Hydroxide,溶剂黄146体系中,用 水 作为反应溶剂,化学反应生成 2-氨基-6-氯苯并噻唑
参考文献:In Vitrobiological Investigations Of Novel Piperazine Based Heterocycles
标题:In Vitrobiological Investigations Of Novel Piperazine Based Heterocycles
摘要:本研究采用简单高效的方法合成了 11 种 N-苯基和 11 种 N-苯并噻唑基-2-(4-(2,3,4-三甲氧基苄基)哌嗪-1-基)乙酰胺.测试了这 22 种新型化合物对两种革兰氏阳性菌,三种革兰氏阴性菌,两种真菌和结核分枝杆菌 H37Rv 的体外生物效力.生物测定结果表明,大多数 N-苯并噻唑取代的哌嗪衍生物具有中等至非常好的生物效力,其 Mic 值令人鼓舞.本文讨论了芳基乙酰胺分子上是否存在各种吸电子或供电子官能团对不同生物测定结果的影响.
DOI:10.3184/174751914X14116443659287

海关参考信息

专利信息


专利号:US-6531470-B1
优先权日:1998-01-23
标题:Oxazolidinone combinatorial libraries, compositions and methods of preparation
发明人：GORDEEV MIKHAIL F; LUEHR GARY W; PATEL DINESH V; NI ZHI-JIE; GORDON ERIC
权利人:UPJOHN CO
摘要:Oxazolidinones and methods for their synthesis are provided. Also provided are combinatorial libraries comprising oxazolidinones, and methods to prepare the libraries. Further provided are methods of making biologically active oxazolidinones as well as pharmaceutically acceptable compositions comprising the oxazolidinones. The methods of library preparation include the attachment of oxazolidinones to a solid support. The methods of compound preparation in one embodiment involve the reaction of an iminophosphorane with a carbonyl containing polymeric support.

专利号:US-4257942-A
优先权日:1977-10-06
标题:New water-insoluble azo dyes
发明人：DEFEO FRANCESCO; CIPOLLI ROBERTO
权利人:ACNA
摘要:The present invention relates to the synthesis of new dyes having the following general formula: wherein: D is the residue of a diazotizable component of the carbocyclic or heterocyclic series X is an ethylene group, optionally substituted by halogen-methyl, alkyl C1-C4, aryl, aralkyl or CH2OCO(HN)nR (wherein R and n have the meanings hereinafter defined); R is alkyl C1-C8 optionally substituted by halogen, CN,COOH; aryl optionally substituted by one or more atoms of halogen, alkyl C1-C4, alkoxyl C1-C4; alkoxyl C1-C4; alkoxyl C1-C8; Aryloxy; aralkoxy; cycloalkoxy; aralkyl; naphthyl optionally substituted by halogen; alkenyl C2-C8, optionally substituted by halogen, CN, COOH; R1 and R2, either like or unlike each other, may be alkyl C1-C4 optionally substituted by halogen or CN groups; aralkyl; R3 is H; halogen, alkyl C1-C4; alkoxyl C1-C4, optionally substituted. n is 0 or 1.

专利号:US-6562844-B2
优先权日:1998-01-23
标 题:Oxazolidinone combinatorial libraries, compositions and methods of preparation
发明人：GORDEEV MIKHAIL F; LUEHR GARY W; PATEL DINESH V; NI ZHI-JIE; GORDON ERIC
权利人:UPJOHN CO
摘要:Oxazolidinones and methods for their synthesis are provided. Also provided are combinatorial libraries comprising oxazolidinones, and methods to prepare the libraries. Further provided are methods of making biologically active oxazolidinones as well as pharmaceutically acceptable compositions comprising the oxazolidinones. The methods of library preparation include the attachment of oxazolidinones to a solid support. The methods of compound preparation in one embodiment involve the reaction of an iminophosphorane with a carbonyl containing polymeric support.

专利号:US-7002020-B1
优先权日:1998-01-23
标题:Oxazolidinone combinatorial libraries, compositions and methods of preparation
发明人：GORDEEV MIKHAIL F; LUEHR GARY W; PATEL DINESH V
权利人:UPJOHN CO
摘要:Oxazolidinones and methods for their synthesis are provided. Also provided are combinatorial libraries comprising oxazolidinones, and methods to prepare the libraries. Further provided are methods of making biologically active oxazolidinones as well as pharmaceutically acceptable compositions comprising the oxazolidinones. The methods of library preparation include the attachment of oxazolidinones to a solid support. The methods of compound preparation in one embodiment involve the reaction of an iminophosphorane with a carbonyl containing polymeric support.

专利号:US-5663149-A
优先权日:1994-12-13
标 题:Human cancer inhibitory pentapeptide heterocyclic and halophenyl amides
发明人：PETTIT GEORGE R; SRIRANGAM JAYARAM K; KANTOCI DARKO
权利人:UNIV ARIZONA
摘要:The synthesis and elucidation of nineteen heterocyclic or halophenyl amideerivatives of dolastatin 10 are disclosed. These compounds and the methods of producing those compounds offer demonstrated significant in vitro activity against several human cancer cell lines. These compounds and the methods of producing those compounds offer a commercially viable alternative to natural and synthetic dolastatin 10.

专利号:CN-108623537-B
优先权日:2017-05-24
标题:Synthesis and application of aromatic amine acetylcholinesterase inhibitors containing amine side chain

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主要参考文献

参考标题:An Efficient One-Pot Synthesis Of 2-Aminobenzothiazoles From Substituted Anilines Using Benzyltrimethylammonium Dichloroiodate And Ammonium Thiocyanate In Dmso:H2O
作者:Reuben Dass,Matt A. Peterson |发布日期:2021.10
摘要:And Ammonium Thiocyanate (1.0 Equiv) In Dmso:H2O (9:1) At 70 °C Gave The Corresponding 2-Aminobenzothiazoles In Excellent Isolated Yields (75-97%; Ave. Yield For All Substrates = 90%). The Reaction Worked Well For 2(4)-Mono-, 2,4-Di-, Or 3,4,5-Tri-Substituted Anilines, And A Wide Range Of Both Electron Donating Groups (Meo, Ho, Cf3O, Me) And Electron Withdrawing Groups (No2, Cn, Co2Et, Co2H, Cl, F)

合成参考文献


参考文献:10.1126/sciadv.abf8711
摘要:Schuller M, Correy GJ, Gahbauer S, Fearon D, Wu T, Díaz RE, Young ID, Carvalho Martins L, Smith DH, Schulze-Gahmen U, Owens TW, Deshpande I, Merz GE, Thwin AC, Biel JT, Peters JK, Moritz M, Herrera N, Kratochvil HT; QCRG Structural Biology Consortium, Aimon A, Bennett JM, Brandao Neto J, Cohen AE, Dias A, Douangamath A, Dunnett L, Fedorov O, Ferla MP, Fuchs MR, Gorrie-Stone TJ, Holton JM, Johnson MG, Krojer T, Meigs G, Powell AJ, Rack JGM, Rangel VL, Russi S, Skyner RE, Smith CA, Soares AS, Wierman JL, Zhu K, O'Brien P, Jura N, Ashworth A, Irwin JJ, Thompson MC, Gestwicki JE, von Delft F, Shoichet BK, Fraser JS, Ahel I. Fragment binding to the Nsp3 macrodomain of SARS-CoV-2 identified through crystallographic screening and computational docking. Sci Adv. 2021 Apr;7(16).
摘要:Journal of Pharmacology and Experimental Therapeutics., 105(486), 1952 []
摘要:Rakitin, O. A., Science of Synthesis, (2007) 31, 966.
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