CAS: 7184-60-3; (1R,2R)-2-((2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-Cyano-8,16-Dihydroxy-9,11,13,15-Tetramethyl-18-Oxooxacyclooctadeca-4,6-Dien-2-yl)Cyclopentane-1-Carboxylic Acid
该化合物是一种该化合物是一种该化合物是一种刺激蛋白质合成的强效抑制剂.它展示了广泛频谱抗微生物活动,特别是针对Borrelia物种的活动,使它成为抗生素研究的复合体.此外,Borrelidin展示了抗生素特性,表明癌症治疗可能应用.它独特的行动机制,针对氨基乙酰-tRNA合成物,将其与其他抗生素区分开来,减少交叉抗生素的可能性.Borrelidin的复杂多氯酸酯结构也使它成为合成和药用化学研究的宝贵主题.然而,它的细胞毒性需要进一步结构优化用于治疗用途.
- 英文名称(1R,2R)-2-((2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-Cyano-8,16-Dihydroxy-9,11,13,15-Tetramethyl-18-Oxooxacyclooctadeca-4,6-Dien-2-yl)Cyclopentane-1-Carboxylic Acid
- 中文名称抗螺旋体链丝菌素
- IUPAC名称(1R,2R)-2-((2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl)cyclopentane-1-carboxylic acid
- 其它别名2-(7-Cyano-8,16-Dihydroxy-9,11,13,15-Tetramethyl-18-Oxooxacyclooctadeca-4,6-Dien-2-yl)-Cyclopentanecarboxylic Acid; Borrelidin; Borrelidine; 2-(7-Cyano-8,16-Dihydroxy-9,11,13,15-Tetramethyl-18-Oxo-1-Oxacyclooctadeca-4,6-Dien-2-yl)Cyclopentane-1-Carboxylic Acid; Cyclopentanecarboxylic Acid, 2-(7-Cyano-8, 16-Dihydroxy-9,11,13,15-Tetramethyl-18-Oxooxacyclooctadeca-4, 6-Dien-2-yl)-
- CAS编号7184-60-3
- MFCD编号:MFCD08276914
- EINECS号:811-923-0
- FDA UNII编号:PWC22KGM2P
- 分子式:C28H43NO6分子量:489.65
- 产品CID: 1707164
- 产品分类原料药 → 抗生素类药物 → 其它抗生素类药
物理性质
- 熔点143-145 °C
- 沸点710.3±60.0 °C at 760 mmHg
- 闪点383.4±32.9 °C
- 密度1.1±0.1 g/cm3
- pKa:4.56±0.40(预测)
- PSA:127.85
- LogP:4.31
- 折射率1.539
- 蒸汽压0.0±5.1 mmHg at 25°C
- 溶解性DMSO: 1 mg/mL
- 外观形态类白色白色至类白色粉末
- 储存条件−20°C
- 产品应用该化合物是血管产生(IC50 = 0.8 NM)的强力抑制剂,在血管内皮细胞中诱发聚变;抑制细菌和EUKARYOTES 中的硫酰-TRNA合成酶;它作为在发芽酵中的CDC28/CLN2抑制剂(IC 50 =24 ΜM);它展示了对恶性疟原虫K1和FCR3菌株(分别为IC50= 1.9 NM 和1.8 NM);其针对急性淋巴性白血病细胞(ALL)的抗药性,引起一种流行性病和介导G1细胞循环阻塞.
MSDS等安全信息
欧盟法规
ECHA物质C&L通报上下游产品
(1'R,1S,2S,2'R,8R,9S,11R,13S,15S,16S)-2-(7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-oxacyclo°Ctadeca-4,6-dien-2-yl)-cyclopentane-1'-carboxylic acid 2-trimethylsilanyl-ethyl ester (1R,2R)-2-((4E,6Z)-(2S,9S,11R,13S,15S,16S)-7-Cyano-16-hydroxy-9,11,13,15-tetramethyl-8,18-dioxo-oxacyclo°Ctadeca-4,6-dien-2-yl)-cyclopentanecarboxylic acid (2S,4R,8S,Z)-9-(tert-butyldiphenylsilyloxy)-2,4,6,8-tetramethylnon-3-en-1-ol 42H66O6SiNC°CF3C42H66O6SiNC°CF3 38H50N4O8C38H50N4O8 35H49NO6C35H49NO6 37H52N2O8C37H52N2O8合成工艺路线路线简述
- 合成目标产物 Borrelidin 主要起始原料 1,2-Cyclopentanedicarboxylic Acid, 4-Oxo-, 1,2-Dimethyl Ester, (1R,2R)-
- (文献来源)合成步骤主要原料 1,2-Cyclopentanedicarboxylic Acid, 4-Oxo-, 1,2-Dimethyl Ester, (1R,2R)-
📜(+)-(S,2E,4E)-2-Bromo-7-Hydroxy-7-((1R,2R)-2-((4 Methoxybenzyloxy)Methyl)Cyclopentyl)Hepta-2,4-Dienenitrile置于2,6-二甲基吡啶,六甲基磷酰三胺,4-二甲氨基吡啶,Sodium Chlorite,Sodium Dihydrogenphosphate,Samarium Diiodide,四丙基高钌酸铵,2-甲基-2-丁烯,4 A Molecular Sieve,4-甲基苯磺酸吡啶,戴斯-马丁氧化剂,氟化氢吡啶,N-甲基吗啉氧化物,2,3-二氯-5,6-二氰基-1,4-苯醌体系中,用 四氢呋喃,乙醇,二氯甲烷,水,叔丁醇,苯 作为反应溶剂,化学反应 63.75H,反应生成 抗螺旋体链丝菌素
参考文献:(-)-硼瑞林的全合成.
标题:(-)-硼瑞林的全合成.
摘要:已经实现了硼瑞林的全合成.我们的合成路线的最大特点是smi(2)介导的分子内reformatsky型反应的两个部分之间酯化后的大环化反应.这两个关键部分是通过螯合控制的氨基甲酸酯化,螯合控制的氢化,立体选择性reformatsky反应和mgbr(2).Et(2)o介导的螯合控制的烯丙基化合成的.[反应:看文字]
DOI:10.1021/ol049356W
供应商参考报价(招募中)
品牌试剂参考报价(招募中)
📌 第三方产品分析报告
主要参考文献
参考标题:Application Of Conformation Design In Acyclic Stereoselection: Total Synthesis Of Borrelidin As The Crystalline Benzene Solvate作者:Stephen Hanessian,Yang,Simon Giroux,Vincent Mascitti,Jianguo Ma,Franck Raeppel |发布日期:2003.11.1
摘要:The Total Synthesis Of (-)-Borrelidin (Treponemycin), A Structurally Distinct 18-Membered Macrolide Antibiotic, Has Been Achieved. It Was Isolated As The Crystalline Benzene Solvate, And Its Structure Was Confirmed By A Single-Crystal X-Ray Analysis. The Deoxypropionate Subunit Consisting Of Four Alternating C-Methyl Groups With A C(4)-C(10) Syn/syn/anti Orientation Was Elaborated By A New Method Of
合成参考文献
参考文献:10.1111/j.1365-2958.2004.04090.x
摘要:Olano C, Moss SJ, Braña AF, Sheridan RM, Math V, Weston AJ, Méndez C, Leadlay PF, Wilkinson B, Salas JA. Biosynthesis of the angiogenesis inhibitor borrelidin by Streptomyces parvulus Tü4055: insights into nitrile formation†. Molecular Microbiology. 2004 May 21;52(6):1745–56. doi: 10.1111/j.1365-2958.2004.04090.x.
摘要:S6 | ITNANTIBIOTIC | Antibiotic List from the ITN MSCA ANSWER | DOI:10.5281/zenodo.2621956
摘要:Journal of Clinical Investigation., 28(1047), 1949
摘要:Antibiotics: Origin, Nature, and Properties, Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978, 2(1198), 1978
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