pulicatin B | 1257057-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: pulicatin B
• 英文别名: Pulicatin B；2-[(4S,5S)-4-(hydroxymethyl)-5-methyl-4,5-dihydro-1,3-thiazol-2-yl]phenol
• CAS: 1257057-13-8
• 化学式: C₁₁H₁₃NO₂S
• 分子量: 223.296
• InChiKey: ZVWPMYHMXUXIMC-CBAPKCEASA-N

物化性质

• 沸点：
  400.1±51.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  78.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  pulicatin B 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 吡啶 作用下， 反应 12.0h， 生成
  参考文献：
  名称：

  Pulicatins A−E, Neuroactive Thiazoline Metabolites from Cone Snail-Associated Bacteria

  摘要：

  The cone snail Conus pulicarius from the Philippines provides a specific habitat for actinomycetes and other bacteria. A phenotypic screen using primary cultures of mouse dorsal root ganglion neurons revealed that one C. pulicarius associate, Streptomyces sp. CP32, produces a series of natural products that enhance or diminish whole-cell Ca2+ flux. These compounds include known thiazoline compounds and a series of new derivatives, pulicatins A-E (6-10). Individual compounds were shown to hind to a series of human receptors, with selective binding to the human serotonin 5-HT2B receptor. Here, we report the structure elucidation of the new compounds and results of the neurological assays.

  DOI：

  10.1021/np100588c
• 作为产物：
  描述：

  N-(o-hydroxybenzoyl)-L-threonine methyl ester 在 劳森试剂 、 sodium tetrahydroborate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 0.02h， 生成 pulicatin B 、 2-[(4R,5R)-4-(hydroxymethyl)-5-methyl-4,5-dihydro-1,3-thiazol-2-yl]phenol
  参考文献：
  名称：

  Modulating the Serotonin Receptor Spectrum of Pulicatin Natural Products

  摘要：

  Serotonin (5-HT) receptors are important in health and disease, but the existence of 14 subtypes necessitates selective ligands. Previously, the pulicatins were identified as ligands that specifically bound to the subtype 5-HT2B in the 500 nM to 10 mu M range and that exhibited in vitro effects on cultured mouse neurons. Here, we examined the structure activity relationship of 30 synthetic and natural pulicatin derivatives using binding, receptor functionality, and in vivo assays. The results reveal the 2-arylthiazoline scaffold as a tunable serotonin receptor-targeting pharmacophore. Tests in mice show potential antiseizure and antinociceptive activities at high doses without motor impairment.

  DOI：

  10.1021/acs.jnatprod.7b00317

文献信息

• METHODS AND COMPOSITIONS RELATED TO NEUROACTIVE THIAZOLINE COMPOUNDS
  申请人：Schmidt Eric W.

  公开号：US20140018400A1

  公开（公告）日：2014-01-16

  In one aspect, the invention relates to compounds having a general structure: and methods of using same to modulate calcium release. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  在某个方面，本发明涉及具有一般结构的化合物：以及使用同样的方法来调节钙释放。本摘要旨在作为扫描工具，用于在特定技术领域进行搜索，不旨在限制本发明。
• US9751847B2
  申请人：——

  公开号：US9751847B2

  公开（公告）日：2017-09-05
• Modulating the Serotonin Receptor Spectrum of Pulicatin Natural Products
  作者：Zhenjian Lin、Misty D. Smith、Gisela P. Concepcion、Margo G. Haygood、Baldomero M. Olivera、Alan Light、Eric W. Schmidt

  DOI：10.1021/acs.jnatprod.7b00317

  日期：2017.8.25

  Serotonin (5-HT) receptors are important in health and disease, but the existence of 14 subtypes necessitates selective ligands. Previously, the pulicatins were identified as ligands that specifically bound to the subtype 5-HT2B in the 500 nM to 10 mu M range and that exhibited in vitro effects on cultured mouse neurons. Here, we examined the structure activity relationship of 30 synthetic and natural pulicatin derivatives using binding, receptor functionality, and in vivo assays. The results reveal the 2-arylthiazoline scaffold as a tunable serotonin receptor-targeting pharmacophore. Tests in mice show potential antiseizure and antinociceptive activities at high doses without motor impairment.
• Pulicatins A−E, Neuroactive Thiazoline Metabolites from Cone Snail-Associated Bacteria
  作者：Zhenjian Lin、Rowena R. Antemano、Ronald W. Hughen、Ma. Diarey B. Tianero、Olivier Peraud、Margo G. Haygood、Gisela P. Concepcion、Baldomero M. Olivera、Alan Light、Eric W. Schmidt

  DOI：10.1021/np100588c

  日期：2010.11.29

  The cone snail Conus pulicarius from the Philippines provides a specific habitat for actinomycetes and other bacteria. A phenotypic screen using primary cultures of mouse dorsal root ganglion neurons revealed that one C. pulicarius associate, Streptomyces sp. CP32, produces a series of natural products that enhance or diminish whole-cell Ca2+ flux. These compounds include known thiazoline compounds and a series of new derivatives, pulicatins A-E (6-10). Individual compounds were shown to hind to a series of human receptors, with selective binding to the human serotonin 5-HT2B receptor. Here, we report the structure elucidation of the new compounds and results of the neurological assays.