2'-O-acetyl-6-O-methyl-3-O-decladinosyl-erythromycin A 11,12-cyclic carbamate | 152235-49-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-O-acetyl-6-O-methyl-3-O-decladinosyl-erythromycin A 11,12-cyclic carbamate
• 英文别名: [(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(1S,2R,5R,6S,7S,8R,9R,11R,13R,14R)-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]-6-methyloxan-3-yl] acetate
• CAS: 152235-49-9
• 化学式: C₃₃H₅₆N₂O₁₁
• 分子量: 656.814
• InChiKey: LVBSJJSKIJNUNH-WSTFHHRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  46
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  159
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2'-O-acetyl-6-O-methyl-3-O-decladinosyl-erythromycin A 11,12-cyclic carbamate 在 N-氯代丁二酰亚胺 、 二甲基硫 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 106.33h， 生成
  参考文献：
  名称：

  CN114437154

  摘要：

  公开号：
• 作为产物：
  描述：

  在 吡啶 、 三光气 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 2'-O-acetyl-6-O-methyl-3-O-decladinosyl-erythromycin A 11,12-cyclic carbamate
  参考文献：
  名称：

  CN114437154

  摘要：

  公开号：

文献信息

• Decladinosyl-Macrolides With Anti-Inflammatory Activity
  申请人：Culic Ognjen

  公开号：US20080234211A1

  公开（公告）日：2008-09-25

  The present invention relates to novel semi-synthetic macrolides having anti-inflammatory activity. More particularly, the invention relates to 14- and 15-membered macrolides lacking cladinose sugar substituted at the C-3 position, to their pharmaceutically acceptable derivatives, to processes and intermediates for their preparation, to pharmaceutical compositions containing them and to their activity and use in the treatment of inflammatory diseases and conditions in humans and animals, especially those diseases associated with excessive secretion of TNF-α, IL-1, IL-6, IL-8, IL-2 or IL-5; and/or inhibitor of excessive lymphocyte proliferation; and/or excessive granulocyte degranulation.

  本发明涉及具有抗炎活性的新型半合成大环内酯类化合物。更具体地说，本发明涉及在C-3位置缺乏克拉地酮糖取代的14-和15-环内酯类化合物，以及它们的药用可接受衍生物，用于它们的制备的过程和中间体，含有它们的药物组合物，以及它们在治疗人类和动物的炎症性疾病和症状中的活性和用途，特别是那些与过度分泌TNF-α、IL-1、IL-6、IL-8、IL-2或IL-5有关的疾病；和/或抑制过度淋巴细胞增殖；和/或过度粒细胞脱颗粒的抑制剂。
• Synthesis and Antibacterial Activity of a Novel Series of Acylides:  3-<i>O</i>-(3-Pyridyl)acetylerythromycin A Derivatives
  作者：Tetsuya Tanikawa、Toshifumi Asaka、Masato Kashimura、Keiko Suzuki、Hiroyuki Sugiyama、Masakazu Sato、Kazuya Kameo、Shigeo Morimoto、Atsushi Nishida

  DOI：10.1021/jm020568d

  日期：2003.6.1

  A novel series of acylides, 3-O-(aryl)acetylerythromycin A derivatives, were synthesized and evaluated. These compounds have significant potent antibacterial activity against not only Gram-positive pathogens, including inducibly macrolide-lincosamide-streptogramin B (MLSB)-resistant and efflux-resistant strains, but also Gram-negative pathogens, such as H. influenzae. 6,9:11,12-Dicarbonate acylide 47 (FMA0122) was twice as active against H. influenzae than azithromycin, whereas it showed only moderate in vivo efficacy in mouse protection tests. However, the 11,12-carbamate acylide 19 (TEA0929), which showed potent antibacterial activity against almost all of the main causative pathogens of community-acquired pneumonia tested, exhibited excellent in vivo efficacy comparable to those of second-generation macrolides.
• Novel 3-O-carbamoyl erythromycin A derivatives (carbamolides) with activity against resistant staphylococcal and streptococcal isolates
  作者：Thomas V. Magee、Seungil Han、Sandra P. McCurdy、Thuy-Trinh Nguyen、Karl Granskog、Eric S. Marr、Bruce A. Maguire、Michael D. Huband、Jinshan Michael Chen、Timothy A. Subashi、Veerabahu Shanmugasundaram

  DOI：10.1016/j.bmcl.2013.01.067

  日期：2013.3

  A novel series of 3-O-carbamoyl erythromycin A derived analogs, labeled carbamolides, with activity versus resistant bacterial isolates of staphylococci (including macrolide and oxazolidinone resistant strains) and streptococci are reported. An (R)-2-aryl substituent on a pyrrolidine carbamate appeared to be critical for achieving potency against resistant strains. Crystal structures showed a distinct aromatic interaction between the (R)-2-aryl (3-pyridyl for 4d) substituent on the pyrrolidine and G2484 (G2505, Escherichia coli) of the Deinococcus radiodurans 50S ribosome (3.2 angstrom resolution). (C) 2013 Elsevier Ltd. All rights reserved.
• US7910559B2
  申请人：——

  公开号：US7910559B2

  公开（公告）日：2011-03-22