mollamide F | 1393002-32-8

• 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: mollamide F
• 英文别名: (2R,5S,11S,17S,20S,23S)-2-benzyl-20-[(2S)-butan-2-yl]-17-propan-2-yl-25-thia-3,9,15,18,21,26-hexazatetracyclo[21.2.1.05,9.011,15]hexacos-1(26)-ene-4,10,16,19,22-pentone
• CAS: 1393002-32-8
• 化学式: C₃₃H₄₆N₆O₅S
• 分子量: 638.831
• InChiKey: PCJVGSSHAGXUGI-NIGUMGSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  45
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  166
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  胱胺 、 mollamide F 在 盐酸 、 水 作用下， 反应 17.83h， 生成 D-2-amino-3-((2-aminoethyl)disulfanyl)-propanoic acid
  参考文献：
  名称：

  Thiazoline Peptides and a Tris-Phenethyl Urea from Didemnum molle with Anti-HIV Activity

  摘要：

  As part of our screening for anti-HIV agents from marine invertebrates, the MeOH extract of Didemnum molle was tested and showed moderate in vitro anti-HIV activity. Bioassay-guided fractionation of a large-scale extract allowed the identification of two new cyclopeptides, mollamides E and F (1 and 2), and one new tris-phenethyl urea, molleurea A (3). The absolute configurations were established using the advanced Marfey's method. The three compounds were evaluated for anti-HIV activity in both an HIV integrase inhibition assay and a cytoprotective cell-based assay Compound 2 was active in both assays with IC50 values of 39 and 78 mu M, respectively. Compound 3 was active only in the cytoprotective cell-based assay, with an IC50 value of 60 mu M.

  DOI：

  10.1021/np300270p
• 作为产物：
  描述：

  在 3,3,3-膦三基三丙酸 作用下， 以 aq. phosphate buffer 、 水 、 乙腈 为溶剂， 以68 %的产率得到mollamide F
  参考文献：
  名称：

  N-硫酰基-2-巯基乙胺衍生物环脱硫合成含噻唑啉复合肽

  摘要：

  描述了N-硫酰基-2-巯基乙胺自发环脱硫生成噻唑啉及其在高效、无差向异构化含噻唑啉肽合成中的应用。该新方法具有反应条件温和、反应时间短、同时耐受反应性官能团的特点，可以快速获得复杂的含噻唑啉的肽，包括天然产物mollamide F。

  DOI：

  10.1002/anie.202301543

文献信息

• Thiazoline Peptides and a Tris-Phenethyl Urea from <i>Didemnum molle</i> with Anti-HIV Activity
  作者：Zhenyu Lu、Mary Kay Harper、Christopher D. Pond、Louis R. Barrows、Chris M. Ireland、Ryan M. Van Wagoner

  DOI：10.1021/np300270p

  日期：2012.8.24

  As part of our screening for anti-HIV agents from marine invertebrates, the MeOH extract of Didemnum molle was tested and showed moderate in vitro anti-HIV activity. Bioassay-guided fractionation of a large-scale extract allowed the identification of two new cyclopeptides, mollamides E and F (1 and 2), and one new tris-phenethyl urea, molleurea A (3). The absolute configurations were established using the advanced Marfey's method. The three compounds were evaluated for anti-HIV activity in both an HIV integrase inhibition assay and a cytoprotective cell-based assay Compound 2 was active in both assays with IC50 values of 39 and 78 mu M, respectively. Compound 3 was active only in the cytoprotective cell-based assay, with an IC50 value of 60 mu M.
• Synthesis of Complex Thiazoline‐Containing Peptides by Cyclodesulfhydration of<i>N</i>‐Thioacyl‐2‐Mercaptoethylamine Derivatives
  作者：Marat Meleshin、Lukas Koch、Christoph Wiedemann、Mike Schutkowski

  DOI：10.1002/anie.202301543

  日期：2023.6.19

  N-thioacyl-2-mercaptoethylamines to thiazolines and its application to the efficient and epimerization-free synthesis of thiazoline-containing peptides is described. The novel method features mild reaction conditions and short reaction times while tolerating reactive functional groups, providing rapid access to complex thiazoline-containing peptides including the natural product mollamide F.

  描述了N-硫酰基-2-巯基乙胺自发环脱硫生成噻唑啉及其在高效、无差向异构化含噻唑啉肽合成中的应用。该新方法具有反应条件温和、反应时间短、同时耐受反应性官能团的特点，可以快速获得复杂的含噻唑啉的肽，包括天然产物mollamide F。