[(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-4-二甲基氨基-5-羟基-6-[[(4R,5S,6S,7R,9R,11E,13E,16R)-5-甲氧基-9,16-二甲基-2,10-二氧代-7-(2-氧代乙基)-4-丙酰氧基-1-氧杂环十六碳-11,13-二烯-6-基]氧基]-2-甲基四氢吡喃-3-基]氧基-4-羟基-2,4-二甲基四氢吡喃-3-基]丙酸酯 | 36025-69-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: [(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-4-二甲基氨基-5-羟基-6-[[(4R,5S,6S,7R,9R,11E,13E,16R)-5-甲氧基-9,16-二甲基-2,10-二氧代-7-(2-氧代乙基)-4-丙酰氧基-1-氧杂环十六碳-11,13-二烯-6-基]氧基]-2-甲基四氢吡喃-3-基]氧基-4-羟基-2,4-二甲基四氢吡喃-3-基]丙酸酯
• 英文名称: midecamycin A3
• 英文别名: [(4R,5S,6S,7R,9R,11E,13E,16R)-6-[(2S,3R,4R,5S,6R)-4-(dimethylamino)-3-hydroxy-5-[(2S,4R,5S,6S)-4-hydroxy-4,6-dimethyl-5-propanoyloxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-5-methoxy-9,16-dimethyl-2,10-dioxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-4-yl] propanoate
• CAS: 36025-69-1
• 化学式: C₄₁H₆₅NO₁₅
• 分子量: 811.965
• InChiKey: POOQYAXQHUANTP-BCGBQJBESA-N

物化性质

• 熔点：
  122-125°
• 比旋光度：
  D22 -44° (c = 1 in ethanol)
• 沸点：
  876.1±65.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  57
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  203
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  [(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-4-二甲基氨基-5-羟基-6-[[(4R,5S,6S,7R,9R,11E,13E,16R)-5-甲氧基-9,16-二甲基-2,10-二氧代-7-(2-氧代乙基)-4-丙酰氧基-1-氧杂环十六碳-11,13-二烯-6-基]氧基]-2-甲基四氢吡喃-3-基]氧基-4-羟基-2,4-二甲基四氢吡喃-3-基]丙酸酯 在 盐酸 、 silver perchlorate 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 16.08h， 生成 [(4R,5S,6S,7R,9R,11E,13E,16R)-6-[(2S,3R,4R,5S,6R)-4-(dimethylamino)-5-[(2S,4R,5S,6S)-5-hexoxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3-hydroxy-6-methyloxan-2-yl]oxy-5-methoxy-9,16-dimethyl-2,10-dioxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-4-yl] propanoate
  参考文献：
  名称：

  Cladinose Analogues of Sixteen-membered Macrolide Antibiotics. I. Synthesis of 4-0-Alkyl-L-cladinose Analogues via Glycosylation.

  摘要：

  本文描述了具有4-O-烷基-α-L-纤维基中性糖部分的十六元大环内酯的合成与生物学评价。这九种新颖衍生物是通过与1-硫代糖的糖基化反应合成的。其中活性最强的衍生物在体外大鼠血浆中显示出延长的抗菌活性，并具有改善的药代动力学特性。

  DOI：

  10.7164/antibiotics.49.582

文献信息

• [EN] 14-MEMBERED MACROLIDES DERIVED FROM LEUCOMYCINS<br/>[FR] MACROLIDES A 14 ELEMENTS ISSUS DE LEUCOMYCINES
  申请人：ENANTA PHARM INC

  公开号：WO2002060912A1

  公开（公告）日：2002-08-08

  Novel 14-Membered Macrolides derived from Leucomycins comprising a therapeutically effective amount of a compound of the invention in combination with a pharmaceutically acceptable carrier, a method for treating bacterial infections by administering to a mammal a pharmaceutical composition comprising a therapeutically effective amount of a compound of the invention and processes for the preparation of such compounds.

  由Leucomycins衍生的14元大环内酯类小分子化合物，与药学上可接受的载体组合成治疗有效量的药物组合物，用于治疗细菌感染的方法是向哺乳动物施用包含治疗有效量的该化合物的制药组合物，并且还包括制备这种化合物的工艺。
• Process for producing 3-deacylated derivatives of a 16-membered macrolide antibiotic, microorganism to be used therefor and novel macrolide antibiotic
  申请人：MEIJI SEIKA KAISHA LTD.

  公开号：EP0526906A1

  公开（公告）日：1993-02-10

  A method of producing a 3-deacylated derivative of a 16-membered macrolide antibiotic using a microorganism belonging to the genus Phialophora or Preussia which comprises incubating said microorganism with a 16- membered macrolide antibiotic in a medium containing nutritional sources commonly used for incubating microorganisms, isolating a 3-deacylated derivative from the incubation medium, a microorganism to be used for the above method and a novel macrolide antibiotic.

  一种利用属于 Phialophora 或 Preussia 属的微生物生产 16 位大环内酯抗生素的 3-脱酰基衍生物的方法，该方法包括将所述微生物与 16 位大环内酯抗生素在含有培养微生物常用营养源的培养基中培养，从培养基中分离出 3-脱酰基衍生物、用于上述方法的微生物和新型大环内酯抗生素。
• 16-Membered macrolide derivative having sustained antibacterial activity in plasma, synthesic intermediate thereof and process for producing the same
  申请人：MEIJI SEIKA KAISHA LTD.

  公开号：EP0560147A1

  公开（公告）日：1993-09-15

  16-membered macrolide compounds wherein both of hydroxyl groups at the 3''- and 4''-positions form ether bonds together with two alkyl groups which are either the same or different from each other is useful as an antibacterial agent. The macrolide compounds represented by formula (I) are prepared by chemically modifying midecamycin A₃ to obtain a synthesis intermediate of the formula (II), which is further chemically modified.

  16 元大环内酯化合物（其中 3''-和 4''-位上的羟基与两个相同或不同的烷基一起形成醚键）可用作抗菌剂。 式(I)代表的大环内酯化合物是通过化学修饰米德霉素 A₃，得到式(II)的合成中间体，再对其进行化学修饰而制备的。
• 14-membered macrolides derived from leucomycins
  申请人：——

  公开号：US20020128212A1

  公开（公告）日：2002-09-12

  There is described a novel class of ring contracted 14-membered macrolides, and pharmaceutically acceptable salts, esters and prodrugs thereof, having antibacterial activity, compositions comprising a therapeutically effective amount of a compound of the invention in combination with a pharmaceutically acceptable carrier as well as a method for treating bacterial infections by administering to a mammal a pharmaceutical composition containing a therapeutically effective amount of a compound of the invention. There are also described synthetic processes for preparing the compounds of the invention

  本发明描述了一类具有抗菌活性的新型缩环 14 元大环内酯及其药学上可接受的盐、酯和原药，包含治疗有效量的本发明化合物与药学上可接受的载体的组合物，以及一种通过向哺乳动物施用包含治疗有效量的本发明化合物的药物组合物来治疗细菌感染的方法。还描述了制备本发明化合物的合成工艺
• BICYCLIC LEUCOMYCINS
  申请人：——

  公开号：US20020160966A1

  公开（公告）日：2002-10-31

  Bicyclic leucomycins and pharmaceutically acceptable compositions comprising a therapeutically effective amount of a compound of the invention in combination with a pharmaceutically acceptable carrier, a method for treating bacterial infections by administering to a mammal a pharmaceutical composition containing a therapeutically-effective amount of a compound of the invention, and processes for the preparation of such compounds

  双环亮菌甲素和包含治疗有效量的本发明化合物与药学上可接受的载体的药学上可接受的组合物，通过向哺乳动物施用包含治疗有效量的本发明化合物的药物组合物治疗细菌感染的方法，以及制备此类化合物的工艺流程