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10,11-anhydro-2',4''-di-O-acetyl-12-O-(imidazol-1-ylcarbonyl)-6-O-methylerythromycin A | 217977-00-9

分子结构分类

有机化合物 - 有机氧化合物

中文名称

——

中文别名

——

英文名称

10,11-anhydro-2',4''-di-O-acetyl-12-O-(imidazol-1-ylcarbonyl)-6-O-methylerythromycin A

英文别名

2,4-di-O-acetyl-10,11-anhydro-12-O-imidazolylcarbonyl-6-O-methylerythromycin A；10,11-anhydro-2',4"-di-O-acetyl-12-O-imidazolylcarbonyl-6-O-methylerythromycin A；[(2R,3S,4E,7R,9R,10R,11S,12S,13R)-10-[(2S,3R,4S,6R)-3-acetyloxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-12-[(2R,4R,5S,6S)-5-acetyloxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-2-ethyl-9-methoxy-3,5,7,9,11,13-hexamethyl-6,14-dioxo-1-oxacyclotetradec-4-en-3-yl] imidazole-1-carboxylate

10,11-anhydro-2',4''-di-O-acetyl-12-O-(imidazol-1-ylcarbonyl)-6-O-methylerythromycin A化学式

CAS

217977-00-9

化学式

C₄₆H₇₃N₃O₁₅

mdl

——

分子量

908.097

InChiKey

JEICBTQWWGVABK-FNTWAYBDSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

877.8±75.0 °C(Predicted)
密度：

1.23±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

5
重原子数：

64
可旋转键数：

14
环数：

4.0
sp3杂化的碳原子比例：

0.78
拓扑面积：

199
氢给体数：

0
氢受体数：

17

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
——	[(2S,3R,4S,6R)-2-[[(3R,4S,5S,6R,7R,9R,11E,13S,14R)-4-[(2R,4R,5S,6S)-5-acetyloxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-1-oxacyclotetradec-11-en-6-yl]oxy]-4-(dimethylamino)-6-methyloxan-3-yl] acetate	438046-02-7	C₄₂H₇₁NO₁₄	814.024
——	2',4''-di-O-acetyl-6-O-methylerythromycin A	152235-55-7	C₄₂H₇₃NO₁₅	832.039
克拉霉素	clarithromycin	81103-11-9	C₃₈H₆₉NO₁₃	747.965

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	[(2S,3R,4S,6R)-2-[[(1S,2R,5R,6S,7S,8R,9R,11R,13R,14R)-6-[(2R,4R,5S,6S)-5-acetyloxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-15-(4-azidobutyl)-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-4,12,16-trioxo-3,17-dioxa-15-azabicyclo[12.3.0]heptadecan-8-yl]oxy]-4-(dimethylamino)-6-methyloxan-3-yl] acetate	849407-73-4	C₄₇H₇₉N₅O₁₅	954.169
——	[(2S,3R,4S,6R)-2-[[(1S,2R,5R,6S,7S,8R,9R,11R,13R,14R)-6-[(2R,4R,5S,6S)-5-acetyloxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-15-(2-aminoethyl)-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-4,12,16-trioxo-3,17-dioxa-15-azabicyclo[12.3.0]heptadecan-8-yl]oxy]-4-(dimethylamino)-6-methyloxan-3-yl] acetate	213330-00-8	C₄₅H₇₇N₃O₁₅	900.117
——	[(2S,3R,4S,6R)-2-[[(1S,2R,5R,6S,7S,8R,9R,11R,13R,14R)-6-[(2R,4R,5S,6S)-5-acetyloxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-15-(2-amino-2-methylpropyl)-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-4,12,16-trioxo-3,17-dioxa-15-azabicyclo[12.3.0]heptadecan-8-yl]oxy]-4-(dimethylamino)-6-methyloxan-3-yl] acetate	374752-09-7	C₄₇H₈₁N₃O₁₅	928.171
——	4''-O-acetyl-11-amino-11-N-(2-aminoethyl)-11-deoxy-6-O-methylerythromycin A 11,12-cyclic carbamate	208456-29-5	C₄₃H₇₅N₃O₁₄	858.08
——	4''-O-acetyl-11-amino-11-N-(3-aminopropyl)-11-deoxy-6-O-methylerythromycin A 11,12-cyclic carbamate	208456-43-3	C₄₄H₇₇N₃O₁₄	872.107
——	[(2S,3R,4S,6R)-2-[[(1S,2R,5R,6S,7S,8R,9R,11R,13R,14R)-6-[(2R,4R,5S,6S)-5-acetyloxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-15-[3-[5-[(3,5-dichloropyridin-4-yl)carbamoyl]-2-methoxyphenoxy]propyl]-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-4,12,16-trioxo-3,17-dioxa-15-azabicyclo[12.3.0]heptadecan-8-yl]oxy]-6-methyl-4-(methylamino)oxan-3-yl] acetate	1266348-04-2	C₅₈H₈₄Cl₂N₄O₁₈	1196.23
——	[(2S,3R,4S,6R)-2-[[(1S,2R,5R,6S,7S,8R,9R,11R,13R,14R)-15-(4-azidobutyl)-2-ethyl-6-hydroxy-9-methoxy-1,5,7,9,11,13-hexamethyl-4,12,16-trioxo-3,17-dioxa-15-azabicyclo[12.3.0]heptadecan-8-yl]oxy]-4-(dimethylamino)-6-methyloxan-3-yl] acetate	849407-74-5	C₃₇H₆₃N₅O₁₁	753.934
——	N-(3,5-dichloropyridin-4-yl)-3-[3-[(1S,2R,5R,6S,7S,8R,9R,11R,13R,14R)-2-ethyl-6-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-8-[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]oxy-9-methoxy-1,5,7,9,11,13-hexamethyl-4,12,16-trioxo-3,17-dioxa-15-azabicyclo[12.3.0]heptadecan-15-yl]propoxy]-4-methoxybenzamide	1266348-05-3	C₅₄H₈₀Cl₂N₄O₁₆	1112.15
——	2',4''-di-O-acetyl-11-amino-9-deoxo-11-deoxy-9,11-N-(2,2-dimethyl)nitriloethano-6-O-methylerythromycin A 11,12-cyclic carbamate	374752-18-8	C₄₇H₇₉N₃O₁₄	910.156
——	4''-O-acetyl-11-amino-9-deoxo-11-deoxy-9,11-N-nitriloethano-6-O-methylerythromycin A 11,12-cyclic carbamate	374752-14-4	C₄₃H₇₃N₃O₁₃	840.065
——	N-[(2S,3R,4S,6R)-2-[[(1S,2R,5R,6S,7S,8R,9R,11R,13R,14R)-15-[3-[5-[(3,5-dichloropyridin-4-yl)carbamoyl]-2-methoxyphenoxy]propyl]-2-ethyl-6-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-9-methoxy-1,5,7,9,11,13-hexamethyl-4,12,16-trioxo-3,17-dioxa-15-azabicyclo[12.3.0]heptadecan-8-yl]oxy]-3-hydroxy-6-methyloxan-4-yl]-N-methylmorpholine-4-carboxamide	1266347-95-8	C₅₉H₈₇Cl₂N₅O₁₈	1225.27
——	11-N-(4-azido-butyl)-6-O-methyl-5-(2-acetyl-desosamynyl)-3-oxo-erythronolide A 11,12-carbamate	760981-81-5	C₃₇H₆₁N₅O₁₁	751.918
——	11-amino-11-N-(2-aminopropyl)-11-deoxy-5-O-desosaminyl-6-O-methylerythronolide A 11,12-cyclic carbamate	374898-09-6	C₃₄H₆₁N₃O₁₀	671.872
——	11-amino-11-N-(2-aminopropyl)-11-deoxy-5-O-desosaminyl-6-O-methylerythronolide A 11,12-cyclic carbamate	374898-08-5	C₃₄H₆₁N₃O₁₀	671.872
——	11-N-(4-azido-butyl)-6-O-methyl-5-O-desosaminyl-3-oxo-erythronolide A 11,12-carbamate	849407-75-6	C₃₅H₅₉N₅O₁₀	709.881
——	2'-O-acetyl-11-amino-9-deoxo-11-deoxy-9,11-N-nitriloethano-5-O-desosaminyl-6-O-methylerythronolide A 11,12-cyclic carbamate	152235-16-0	C₃₅H₅₉N₃O₁₀	681.868
——	[(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(2R,4R,5R,6R,8R,11R,12S,19R,20R)-11-ethyl-4-methoxy-2,4,6,8,12,19-hexamethyl-7,9,14-trioxo-10,13-dioxa-15,18-diazatricyclo[10.6.2.015,20]icos-1(18)-en-5-yl]oxy]-6-methyloxan-3-yl] acetate	374752-20-2	C₃₅H₅₇N₃O₁₀	679.852
——	11-N-(4-azido-butyl)-6-O-methyl-5-(2,4-dibenzoyl-3N-Fmoc-mycaminosyl)-3-oxo-erythronolide A 11,12-carbamate	760981-87-1	C₆₂H₇₃N₅O₁₅	1128.29
——	11-amino-9-deoxo-11-deoxy-5-O-desosaminyl-9-,11-N-nitriloethano-6-O-methylerythronolide A 11,12-cyclic carbamate	152235-15-9	C₃₃H₅₇N₃O₉	639.83
——	11-amino-9-deoxo-3,11-dideoxy-9,11-N-nitriloethano-3-oxo-5-O-desosaminyl-6-O-methylerythronolide A 11,12-cyclic carbamate	153954-82-6	C₃₃H₅₅N₃O₉	637.814
——	11-amino-9-deoxo-11-deoxy-9,11-N-(2R-methyl)nitriloethano-5-O-desosaminyl-6-O-methylerythronolide A 11,12-cyclic carbamate	374752-16-6	C₃₄H₅₉N₃O₉	653.857
——	11-amino-9-deoxo-11-deoxy-9,11-N-(2S-methyl)nitriloethano-5-O-desosaminyl-6-O-methylerythronolide A 11,12-cyclic carbamate	374752-17-7	C₃₄H₅₉N₃O₉	653.857
索利霉素	solithromycin	760981-83-7	C₄₃H₆₅FN₆O₁₀	845.022

反应信息

作为反应物：

描述：

10,11-anhydro-2',4''-di-O-acetyl-12-O-(imidazol-1-ylcarbonyl)-6-O-methylerythromycin A 在吡啶、盐酸、甲醇、 N-碘代丁二酰亚胺、 sodium azide 、 2,6-二叔丁基吡啶、草酰氯、 silver trifluoromethanesulfonate 、二甲基亚砜、三乙胺作用下，以甲醇、二氯甲烷、 N,N-二甲基甲酰胺为溶剂，生成

参考文献：

名称：

新型糖修饰的酮内酯抗生素的有效进入

摘要：

一种新的高效酮内酯糖苷配基途径，为酮内酯抗生素的5 - O-糖基修饰提供了基础。结合有效的铜催化三唑形成反应，合成了一系列新型有效的酮内酯抗生素。

DOI：

10.1016/j.tetlet.2005.01.023
作为产物：

描述：

克拉霉素在 4-二甲氨基吡啶、 sodium hydride 作用下，以四氢呋喃、二氯甲烷、 N,N-二甲基甲酰胺为溶剂，反应 51.5h，生成 10,11-anhydro-2',4''-di-O-acetyl-12-O-(imidazol-1-ylcarbonyl)-6-O-methylerythromycin A

参考文献：

名称：

Synthesis and Antibacterial Activity of the Tricyclic Ketolides TE-802 and Its Analogs.

摘要：

新型 6-O 甲基三环酮类化合物 TE-802 及其类似物是通过两个连续的环化反应合成的：分子内迈克尔加成反应生成 11，12-环氨基甲酸酯；分子内脱水反应生成 9，11-二氮杂庚烯环。这些新的三环酮烷类化合物不仅对红霉素敏感菌株，而且对耐红霉素的金黄色葡萄球菌和肺炎链球菌都具有良好的体外抗菌活性。

DOI：

10.7164/antibiotics.54.664

点击查看最新优质反应信息

文献信息

Ribosome-Templated Azide–Alkyne Cycloadditions: Synthesis of Potent Macrolide Antibiotics by In Situ Click Chemistry

作者：Ian Glassford、Christiana N. Teijaro、Samer S. Daher、Amy Weil、Meagan C. Small、Shiv K. Redhu、Dennis J. Colussi、Marlene A. Jacobson、Wayne E. Childers、Bettina Buttaro、Allen W. Nicholson、Alexander D. MacKerell、Barry S. Cooperman、Rodrigo B. Andrade

DOI：10.1021/jacs.5b13008

日期：2016.3.9

Over half of all antibiotics target the bacterial ribosome-nature's complex, 2.5 MDa nanomachine responsible for decoding mRNA and synthesizing proteins. Macrolide antibiotics, exemplified by erythromycin, bind the 50S subunit with nM affinity and inhibit protein synthesis by blocking the passage of nascent oligopeptides. Solithromycin (1), a third-generation semisynthetic macrolide discovered by combinatorial

超过一半的抗生素以细菌核糖体复合体为目标，即负责解码 mRNA 和合成蛋白质的 2.5 MDa 纳米机器。以红霉素为代表的大环内酯类抗生素以 nM 亲和力结合 50S 亚基，并通过阻断新生寡肽的通过来抑制蛋白质合成。Solithromycin (1) 是通过组合铜催化点击化学发现的第三代半合成大环内酯，通过将大肠杆菌 70S 核糖体或 50S 亚基与大环内酯功能化叠氮化物 2 和 3-乙炔基苯胺 (3) 前体一起孵育原位合成。核糖体模板化的原位点击方法从二元反应（即一种叠氮化物和一种炔烃）扩展到六组分反应（即叠氮化物2和五种炔烃），并最终扩展到16组分反应（即叠氮化物） 2 和 15 炔烃）。如测量的 Kd 值所示，三唑形成的程度与核糖体对抗 (1,4)-区域异构体的亲和力相关。使用配体竞争饱和位点识别（SILCS）方法的计算分析表明，配体的相对亲和力与不同炔烃引起的大环内酯+去糖胺-核糖
Method of treating tuberculosis

申请人：Falzari Kanakeshwari

公开号：US20050014706A1

公开（公告）日：2005-01-20

Macrolide and ketolides, and compositions containing the same, useful in the treatment of tuberculosis are disclosed. Methods of treating tuberculosis using the macrolides and ketolides, and compositions containing the same, also are disclosed.

揭示了用于治疗结核病的大环内酯类和酮内酯类药物，以及包含它们的组合物。还公开了使用大环内酯类和酮内酯类药物以及包含它们的组合物治疗结核病的方法。
Aqueous Phosphoric Acid as a Mild Reagent for Deprotection of <i>tert</i>-Butyl Carbamates, Esters, and Ethers

作者：Bryan Li、Martin Berliner、Richard Buzon、Charles K.-F. Chiu、Stephen T. Colgan、Takushi Kaneko、Nandell Keene、William Kissel、Tung Le、Kyle R. Leeman、Brian Marquez、Ronald Morris、Lisa Newell、Silke Wunderwald、Michael Witt、John Weaver、Zhijun Zhang、Zhongli Zhang

DOI：10.1021/jo061377b

日期：2006.11.1

an effective, environmentally benign reagent for the deprotection of tert-butyl carbamates, tert-butyl esters, and tert-butyl ethers. The reaction conditions are mild and offer good selectivity in the presence of other acid-sensitive groups, including CBZ carbamates, azetidine, benzyl and methyl esters, TBDMS, and methyl phenyl ethers. The mildness of the reaction is further demonstrated in the synthesis

磷酸水溶液（85重量％）是用于脱保护的有效，环境友好的试剂叔丁基氨基甲酸酯，叔丁基酯，和叔-丁基醚。反应条件温和，在其他酸敏感基团（包括氨基甲酸CBZ，氮杂环丁烷，苄基和甲基酯，TBDMS和甲基苯基醚）存在下，具有良好的选择性。反应的温和性在克拉霉素衍生物4的合成中得到了进一步证明，其中叔酸在环状氨基甲酸酯，内酯，缩酮，乙酸酯和可差向异构的甲基酮官能团存在下，除去丁酯。该反应保留了底物的立体化学完整性。反应产率高，后处理方便。
[EN] NEW MACROLIDES AND THEIR USE<br/>[FR] NOUVEAUX MACROLIDES ET LEUR UTILISATION

申请人：BASILEA PHARMACEUTICA AG

公开号：WO2011018510A1

公开（公告）日：2011-02-17

The invention relates to macrolide compounds of formula (I), the use of said compounds as medicaments, in particular for the treatment or prevention of inflammatory and allergic diseases, pharmaceutical compositions containing said compounds and to processes for their preparation. The invention relates in particular to macrolide compounds with antiinflammatory activity mediated primarily through inhibition of phosphodiesterase 4 (PDE4) which makes them useful for the treatment and/or prevention of inflammatory and allergic diseases such as chronic obstructive pulmonary disease (COPD), asthma, rheumatoid arthritis, atopic dermatitis or inflammatory bowel disease or proliferative diseases such as cancer.

该发明涉及公式（I）的大环内酯化合物，所述化合物的用途为药物，特别用于治疗或预防炎症和过敏性疾病，含有该化合物的药物组合物以及其制备方法。该发明特别涉及具有抗炎活性的大环内酯化合物，主要通过磷酸二酯酶4（PDE4）的抑制介导，使其在治疗和/或预防慢性阻塞性肺疾病（COPD）、哮喘、类风湿关节炎、特应性皮炎或炎症性肠病等炎症和过敏性疾病，以及癌症等增殖性疾病方面具有用途。
Novel tethers in ketolide antibiotics

作者：Takushi Kaneko、Karina Romero、Bryan Li、Richard Buzon

DOI：10.1016/j.bmcl.2007.07.018

日期：2007.9

Novel macrolide antibiotics which contain a methylerie unit between two nitrogen atoms of carbarnate groups or between two nitrogen atoms of one carbarnate and one urea group were synthesized using the Curtius rearrangement. Such linkers were shown to be stable under physiological conditions, and the resulting ketolides show potent in vitro and in vivo activity against macrolide-resistant respiratory pathogens. The SAR of various heterocycles and linkers was established. (C) 2007 Elsevier Ltd. All rights reserved.