similanamide

• 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: similanamide
• 英文别名: cyclo (anthranilic acid-L-Val-D-Leu-L-Ala-N-methyl-L-Leu-D-pipecolic acid)；Similanamide；(11S,14R,17S,20S,23R)-17,21-dimethyl-14,20-bis(2-methylpropyl)-11-propan-2-yl-1,9,12,15,18,21-hexazatricyclo[21.4.0.03,8]heptacosa-3,5,7-triene-2,10,13,16,19,22-hexone
• 化学式: C₃₄H₅₂N₆O₆
• 分子量: 640.823
• InChiKey: MFLJIVQNUIVQOL-BAVZPMSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  46
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  157
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  similanamide 在 盐酸 作用下， 以 水 为溶剂， 反应 24.0h， 生成 L-丙氨酸 、 D-丙氨酸 、 N-甲基-L-亮氨酸
  参考文献：
  名称：

  A New Cyclic Hexapeptide and a New Isocoumarin Derivative from the Marine Sponge-Associated Fungus Aspergillus similanensis KUFA 0013

  摘要：

  从海洋海绵相关真菌Aspergillus similanensis KUFA 0013的培养物乙酸乙酯提取物中分离出一种新的异香豆素衍生物similanpyrone C (1)、一种新的环己肽similanamide (2)和一种新的吡咯并吡喃酮衍生物pyripyropene T (3)。通过一维和二维核磁共振光谱分析确定了化合物的结构，在化合物2的情况下，通过将水解物与d和l氨基酸标准品共注射，利用手性高效液相色谱法分析了其氨基酸成分的立体化学。对化合物2和3进行了体外生长抑制活性评估，分别针对MCF-7（乳腺癌腺癌）、NCI-H460（非小细胞肺癌）和A373（黑色素瘤）细胞系，以及针对参考菌株和环境多重耐药分离株（MRS和VRE）的抗菌活性。只有化合物2对这三种癌细胞系表现出弱活性，并且它们均未显示出抗菌活性。

  DOI：

  10.3390/md13031432
• 作为产物：
  描述：

  在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以10.6 mg的产率得到similanamide
  参考文献：
  名称：

  Structure Revision of Similanamide to PF1171C by Total Synthesis

  摘要：

  The total synthesis of the proposed structure of similanamide, a cyclic hexapeptide recently isolated from the marine sponge-associated fungus Aspergillus similanensis KUFA 0013, was achieved by solid-phase synthesis of a linear precursor and solution-phase macrolactamization. The NMR spectra of our synthetic final product were not identical to those of the isolated material and led us to conclude that similanamide is identical to PF1171C, a previously reported diastereomeric hexapeptide.

  DOI：

  10.1021/acs.jnatprod.5b00643

文献信息

• Structure Revision of Similanamide to PF1171C by Total Synthesis
  作者：Yuichi Masuda、Ren Tanaka、A. Ganesan、Takayuki Doi

  DOI：10.1021/acs.jnatprod.5b00643

  日期：2015.9.25

  The total synthesis of the proposed structure of similanamide, a cyclic hexapeptide recently isolated from the marine sponge-associated fungus Aspergillus similanensis KUFA 0013, was achieved by solid-phase synthesis of a linear precursor and solution-phase macrolactamization. The NMR spectra of our synthetic final product were not identical to those of the isolated material and led us to conclude that similanamide is identical to PF1171C, a previously reported diastereomeric hexapeptide.
• A New Cyclic Hexapeptide and a New Isocoumarin Derivative from the Marine Sponge-Associated Fungus Aspergillus similanensis KUFA 0013
  作者：Chadaporn Prompanya、Carla Fernandes、Sara Cravo、Madalena Pinto、Tida Dethoup、Artur Silva、Anake Kijjoa

  DOI：10.3390/md13031432

  日期：——

  A new isocoumarin derivative, similanpyrone C (1), a new cyclohexapeptide, similanamide (2), and a new pyripyropene derivative, named pyripyropene T (3) were isolated from the ethyl acetate extract of the culture of the marine sponge-associated fungus Aspergillus similanensis KUFA 0013. The structures of the compounds were established based on 1D and 2D NMR spectral analysis, and in the case of compound 2 the stereochemistry of its amino acid constituents was determined by chiral HPLC analysis of the hydrolysate by co-injection with the d and l amino acids standards. Compounds 2 and 3 were evaluated for their in vitro growth inhibitory activity against MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and A373 (melanoma) cell lines, as well as antibacterial activity against reference strains and the environmental multidrug-resistant isolates (MRS and VRE). Only compound 2 exhibited weak activity against the three cancer cell lines, and neither of them showed antibacterial activity.

  从海洋海绵相关真菌Aspergillus similanensis KUFA 0013的培养物乙酸乙酯提取物中分离出一种新的异香豆素衍生物similanpyrone C (1)、一种新的环己肽similanamide (2)和一种新的吡咯并吡喃酮衍生物pyripyropene T (3)。通过一维和二维核磁共振光谱分析确定了化合物的结构，在化合物2的情况下，通过将水解物与d和l氨基酸标准品共注射，利用手性高效液相色谱法分析了其氨基酸成分的立体化学。对化合物2和3进行了体外生长抑制活性评估，分别针对MCF-7（乳腺癌腺癌）、NCI-H460（非小细胞肺癌）和A373（黑色素瘤）细胞系，以及针对参考菌株和环境多重耐药分离株（MRS和VRE）的抗菌活性。只有化合物2对这三种癌细胞系表现出弱活性，并且它们均未显示出抗菌活性。