3,5-dichloro-N-[(2R,3S,4R,6S)-4-hydroxy-6-methoxy-2-methyloxan-3-yl]-1H-pyrrole-2-carboxamide | 182160-51-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,5-dichloro-N-[(2R,3S,4R,6S)-4-hydroxy-6-methoxy-2-methyloxan-3-yl]-1H-pyrrole-2-carboxamide
• CAS: 182160-51-6
• 化学式: C₁₂H₁₆Cl₂N₂O₄
• 分子量: 323.176
• InChiKey: PGVYMKYGWQTPNF-MCOJJJQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-溴苯甲酰氯 、 3,5-dichloro-N-[(2R,3S,4R,6S)-4-hydroxy-6-methoxy-2-methyloxan-3-yl]-1H-pyrrole-2-carboxamide 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 18.0h， 以3.8 mg的产率得到[(2R,3R,4R,6S)-3-[(3,5-dichloro-1H-pyrrole-2-carbonyl)amino]-6-methoxy-2-methyloxan-4-yl] 4-bromobenzoate
  参考文献：
  名称：

  Decatromicins A and B, New Antibiotics Produced by Actinomadura sp. MK73-NF4. II. Structure Determination.

  摘要：

  去卡霉素A和B的结构通过多种核磁共振(NMR)实验的分析得以阐明，这些化合物对抗耐甲氧西林金黄色葡萄球菌(MRSA)具有效抑制作用。通过1H、13C、COSY、HMQC和HMBC NMR光谱确定了平面结构。通过NOESY实验阐明了苷元的相对构型，而绝对结构则通过修正的莫舍尔方法进行确定。糖基部分的绝对结构则通过O-(对溴苯甲酰)衍生物的X射线分析得以确定。

  DOI：

  10.7164/antibiotics.52.787
• 作为产物：
  描述：

  甲醇 、 在 盐酸 作用下， 以 水 为溶剂， 以12.9 mg的产率得到
  参考文献：
  名称：

  Halogenated Spirotetronates from Actinoallomurus

  摘要：

  Two new members of the spirotetronate class, nai414-A and nai414-B, were discovered and isolated from an Actinoallomurus sp. Their structures were established by 1D and 2D NMR, UV, and MS analyses and by chemical degradation. They showed antimicrobial and antitumor activity against Gram-positive bacteria and against human microvascular endothelial cells, respectively. Substituting bromide for chloride ions in the growth medium afforded mono- and dibrominated derivatives.

  DOI：

  10.1021/np300003n

文献信息

• Pyrrolosporin A, a New Antitumor Antibiotic from Micromonospora sp. C39217-R109-7. II. Isolation, Physico-chemical Properties, Spectroscopic Study and X-ray Analysis.
  作者：DANIEL R. SCHROEDER、KIMBERLY L. COLSON、STEVE E. KLOHR、MIKE S. LEE、JAMES A. MATSON、LINDA S. BRINEN、JON CLARDY

  DOI：10.7164/antibiotics.49.865

  日期：——

  Pyrrolosporin A (1) is a new macrolide antitumor antibiotic possessing an unusual spiro-a-acyltetronic acid moiety. The antibiotic was isolated from the fermentation broth of Micromonospora sp. by vacuum liquid chromatography, crystallization and reversed phase HPLC (CIS). The structure was determined by a combination of NMR, MS, IR, UV, X-ray analysis and degradation studies.

  吡咯洛霉素A（1）是一种具有不寻常的螺环α-酰基四氢呋喃酸基团的新型大环抗肿瘤抗生素。该抗生素是通过真空液体色谱法、结晶和反相高效液相色谱法（CIS）从微小芽孢杆菌属的发酵液中分离得到的。其结构是通过NMR、MS、IR、UV、X射线分析及降解研究的组合确定的。
• Decatromicins A and B, New Antibiotics Produced by Actinomadura sp. MK73-NF4. II. Structure Determination.
  作者：ISAO MOMOSE、SEHEI HIROSAWA、HIKARU NAKAMURA、HIROSHI NAGANAWA、HIRONOBU IINUMA、DAISHIRO IKEDA、TOMIO TAKEUCHI

  DOI：10.7164/antibiotics.52.787

  日期：——

  The structures of decatromicins A and B that strongly inhibit the growth of MRSA were elucidated by the analysis of various NMR experiments. The planar structure was determined by 1H, 13C, COSY, HMQC and HMBC NMR spectra. The relative configuration of aglycone was elucidated by NOESY experiments and the absolute structure was determined by application of the modified Mosher's method. The absolute structure of glycosyl moiety was determined by X-ray analysis of the O-(p-bromobenzoyl) derivative.

  去卡霉素A和B的结构通过多种核磁共振(NMR)实验的分析得以阐明，这些化合物对抗耐甲氧西林金黄色葡萄球菌(MRSA)具有效抑制作用。通过1H、13C、COSY、HMQC和HMBC NMR光谱确定了平面结构。通过NOESY实验阐明了苷元的相对构型，而绝对结构则通过修正的莫舍尔方法进行确定。糖基部分的绝对结构则通过O-(对溴苯甲酰)衍生物的X射线分析得以确定。
• Halogenated Spirotetronates from <i>Actinoallomurus</i>
  作者：Carlo Mazzetti、Mirko Ornaghi、Eleonora Gaspari、Silvia Parapini、Sonia Maffioli、Margherita Sosio、Stefano Donadio

  DOI：10.1021/np300003n

  日期：2012.6.22

  Two new members of the spirotetronate class, nai414-A and nai414-B, were discovered and isolated from an Actinoallomurus sp. Their structures were established by 1D and 2D NMR, UV, and MS analyses and by chemical degradation. They showed antimicrobial and antitumor activity against Gram-positive bacteria and against human microvascular endothelial cells, respectively. Substituting bromide for chloride ions in the growth medium afforded mono- and dibrominated derivatives.