CAS: 22733-60-4; Siccanin

该化合物是一种化学化合物,属于被称为alkaloids的天然产品类别,主要来源于某些植物来源,并因其潜在的生物活动而得到注意;锡卡宁展示了藻类的典型特征,包括往往含有氮原子的复杂结构,这种结构有助于其药理特性;该化合物已经研究过其对各种生物系统的影响,包括潜在的抗炎和止痛活动;其溶解性和稳定性可能因溶剂和环境条件而不同;与许多藻类一样,锡卡宁还可能在某些浓度上表现出毒性,需要仔细处理和使用研究及可能的治疗应用;为了充分阐明其在医药或农业中的行动和潜在应用机制,往往需要进一步研究.

结构式图片

上下游产品

(-)-siccanin methyl ether (-)-siccan°Chromene methyl ether (S)-(+)-(2',2'-dimethyl-6'-methylene-1'-cyclohexyl)methanol (S)-(-)-2,2-dimethyl-6-methylene-1-[1'-(phenylthio)methyl]cyclohexane

合成工艺路线路线简述

    📜(R)-5-Methoxy-2,7-Dimethyl-2-Vinylchroman置于platinum(Iv) Oxide 4-二甲氨基吡啶,锰,Sodium Periodate,Disodium Hydrogenphosphate,四氧化锇,正丁基锂,Sodium Amalgam,甲基磺酰胺,碘苯二乙酸,Ad-Mix-β,Titanocene Dichloride,氢气,碘,Sodium Hydride,N-甲基吗啉氧化物,2,3-二氯-5,6-二氰基-1,4-苯醌,乙硫醇钠体系中,用 四氢呋喃,二氯甲烷,水,N,N-二甲基甲酰胺,丙酮,叔丁醇,苯 用作溶剂,20.0 °C,101.33 Kpa 条件下,反应生成西卡宁
    参考文献:(-)-Siccanin的对映选择性仿生全合成.
    标题:(-)-Siccanin的对映选择性仿生全合成.
    摘要:
    Doi:10.1002/anie.200351868

    海关参考信息

    专利信息


    专利号:US-7199128-B2
    优先权日:2005-02-02
    标题 :8-N-substituted-2H-isothiazolo[5,4-b]quinolizine-3,4-diones and related compounds as antiinfective agents
    发明人:BRADBURY BARTON J; WILES JASON ALLAN; DESHPANDE MILIND; WANG QIUPING; HASHIMOTO AKIHIRO; LUCIEN EDLAINE
    权利人:ACHILLION PHARMACEUTICALS INC
    摘要:The invention provides compounds and salts of Formula I and Formula II: n nwhich possess antimicrobial activity. The invention also provides novel synthetic intermediates useful in making compounds of Formula I and Formula II. The variables A 1 , A 8 , R 2 , R 3 , R 5 , R 6 , R 7 , and R 9 are defined herein.n n Certain compounds of Formula I and Formula II disclosed herein are potent and selective inhibitors of bacterial DNA synthesis and bacterial replication. The invention also provides antimicrobial compositions, including pharmaceutical compositions, containing one or more compounds of Formula I or Formula II and one or more carriers, excipients, or diluents. Such compositions may contain a compound of Formula I or Formula II as the only active agent or may contain a combination of compounds of Formula I and/or Formula II and one or more other active agents. The invention also provides methods for treating microbial and protozoal infections in animals.

    专利号:US-2009012071-A1
    优先权日:2007-04-23
    标 题 :4-substituted-1h-isothiazolo[5,4-b][1,4]oxazino[2,3,4-ij]quinoline-7,8(2h,9h)-diones and related compounds as anti-infective agents
    发明人:BRADBURY BARTON JAMES; DESHPANDE MILIND; HASHIMOTO AKIHIRO; KIM HA YOUNG; LUCIEN EDLAINE; PAIS GODWIN; PUCCI MICHAEL JOHN; WANG QIUPING; WILES JASON ALLAN
    权利人:ACHILLION PHARMACEUTICALS INC
    摘要:The present invention provides compounds of the formula that possess antimicrobial activity. Certain compounds provided herein possess potent antibacterial, antiprotozoal, or antifungal activity. Particular compounds provided herein are also potent and/or selective inhibitors of microbial DNA synthesis and reproduction. The invention provides anti-microbial compositions, including pharmaceutical compositions, containing a compound of the invention and one or more or more carriers. The invention provides pharmaceutical compositions containing a 4-substituted- 1 H-isothiazolo[5,4-b][1,4]oxazino[2,3,4-ij]quinoline-7,8(2H,9H)-dione or related compound as the only active agent or in combination with one or more other active agents. The invention provides methods for treating or preventing microbial infections, preferably animals, by administering an effective amount of a 4-substituted- 1 H-isothiazolo[5,4-b][1,4]oxazino[2,3,4-ij]quinoline-7,8(2H,9H)-dione or related compound to an organism suffering from or susceptible to microbial infection. The invention also provides methods of inhibiting microbial growth and survival by applying an effective amount of a 4-substituted- 1 H-isothiazolo[5,4-b][1,4]oxazino[2,3,4-ij]quinoline-7,8(2H,9H)-dione or related compound.

    专利号:US-8946422-B2
    优先权日:2005-07-27
    标题:8-methoxy-9H-isothiazolo[5,4-B]quinoline-3,4-diones and related compounds as anti-infective agents
    发明人:BRADBURY BARTON JAMES; WILES JASON ALLAN; WANG QIUPING; HASHIMOTO AKHIRO; LUCIEN EDLAINE; PAIS GODWIN CLARENCE GILROY; DESHPANDE MILIND; PUCCI MICHEAL JOHN; KIM HA YOUNG
    权利人:BRADBURY BARTON JAMES; WILES JASON ALLAN; WANG QIUPING; HASHIMOTO AKHIRO; LUCIEN EDLAINE; PAIS GODWIN CLARENCE GILROY; DESHPANDE MILIND; PUCCI MICHEAL JOHN; KIM HA YOUNG; ACHILLION PHARMACEUTICALS INC
    摘要:The invention provides compound and salts of Formula I and II, disclosed herein, which includes compounds of Formula A and Formula B: Such compounds possess useful antimicrobial activity. The variables R2, R3, R5, R6, R7, and R9 shown in Formula A and B are defined herein. Certain compounds of Formula I and Formula II disclosed herein are potent and/or selective inhibitors of bacterial DNA synthesis and bacterial replication. The invention also provides antimicrobial compositions, including pharmaceutical compositions, containing one or more compounds of Formula I or Formula II and one or more carriers, excipients, or diluents. Such compositions may contain a compound of Formula I or Formula II as the only active agent or may contain a combination of a compound of Formula I or Formula II and one or more other active agents. The invention also provides methods for treating microbial infections in animals.

    专利号:US-7659399-B2
    优先权日:2005-01-05
    标 题 :1-thia-2,4a-diaza-cyclopenta[b]napththalene-3,4-diones and related compounds as anti-infective agents
    发明人:BRADBURY BARTON JAMES; WILES JASON ALLAN
    权利人:ACHILLION PHARMACEUTICALS INC
    摘要:The invention provides compounds and salts of Formula I and Formula II: n nwhich possess antimicrobial activity. The invention also provides novel synthetic intermediates useful in making compounds of Formula I and Formula II. The variables A 1 , A 8 , R 2 , R 3 , R 5 , R 6 , R 7 , and R 9 are defined herein.n n Certain compounds of Formula I and Formula II disclosed herein are potent and selective inhibitors of bacterial DNA synthesis and bacterial replication. The invention also provides antimicrobial compositions, including pharmaceutical compositions, containing one or more compounds of Formula I or Formula II and one or more carriers, excipients, or diluents. Such compositions may contain a compound of Formula I or Formula II as the only active agent or may contain a combination of a compound of Formula I or Formula II and one or more other active agents. The invention also provides methods for treating microbial infections in animals.

    专利号:EP-1809639-B1
    优先权日:2004-11-11
    标 题 :8a, 9-dihydro-4a-h-isothiazolo[5,4-b] quinoline-3, 4-diones and related compounds as anti-infective agents
    发明人:BRADBURY BARTON JAMES; DESHPANDE MILIND; PUCCI MICHAEL JOHN; WANG QIUPING; WILES JASON ALLAN; SONG YONGSHENG; HASHIMOTO AKIHIRO; LUCIEN EDLAINE
    权利人:ACHILLION PHARMACEUTICALS INC
    摘要:The invention provides compounds and salts of Formula I and Formula II: which possess antimicrobial activity. The invention also provides novel synthetic intermediates useful in making compounds of Formula I and Formula II. The variables n, m, p, RA, RB, A1, R2, R3, R5, R6, R7, A8 and R9 are defined herein. Certain compounds of Formula I and Formula II disclosed herein are potent and/or selective inhibitors of bacterial DNA synthesis and bacterial replication. The invention also provides antimicrobial compositions, including pharmaceutical compositions, containing one or more compounds of Formula I or Formula II and one or more carriers, excipients, or diluents. Such compositions may contain a compound of Formula I or Formula II as the only active agent or may contain a combination of a compound of Formula I or Formula II and one or more other active agents. The invention also provides methods for treating microbial infections in eukaryotes.

    专利号:CN-101208345-B
    优先权日:2005-05-25
    标 题 :(S) -N-methylnaltrexone, method of synthesis and pharmaceutical use thereof

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    主要参考文献


    1: Bellotti MG, Riviera L. Siccanin: a new antifungal antibiotic with antidermatophytic properties. In vitro studies. Chemioterapia. 1985 Dec;4(6):431-3. doi: 10.1093/jb/mvp085. Epub 2009 Jun 8. German.
    10: Naito A. [Tracing the past half century of my microbial transformation studies]. Yakugaku Zasshi. 2000 Oct;120(10):839-48. Review. Japanese. doi: 10.3390/toxins6041193.
    12: Yamaguchi H, Uchida K, Tanaka T, Yamaguchi T. [Therapeutic efficacy of a topical tolnaftate preparation in guinea pig model of tinea pedis]. Jpn J Antibiot. 2001 Jun;54(6):323-30. Japanese. Japanese. Review. Japanese. Italian.

    合成参考文献


    参考文献:10.1126/science.1205216
    摘要:Yuan J, Cheng KC, Johnson RL, Huang R, Pattaradilokrat S, Liu A, Guha R, Fidock DA, Inglese J, Wellems TE, Austin CP, Su XZ. Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets. Science. 2011 Aug 05;333(6043):724–9.
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