marinomycin C | 881020-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: marinomycin C
• 英文别名: (4S,6S,8E,10S,12S,14E,16E,18E,20Z,30S,32S,34E,36S,38S,40E,42E,44E,46E)-6,10,12,26,32,36,38,52-octahydroxy-4,30-bis[(2R)-2-hydroxypropyl]-14,40-dimethyl-3,29-dioxatricyclo[46.4.0.022,27]dopentaconta-1(48),8,14,16,18,20,22(27),23,25,34,40,42,44,46,49,51-hexadecaene-2,28-dione
• CAS: 881020-25-3
• 化学式: C₅₈H₇₆O₁₄
• 分子量: 997.233
• InChiKey: GXBIDOSKEKEFEF-LBJGFFSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  72
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  255
• 氢给体数：
  10
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  marinomycin C 、 乙酸酐 在 吡啶 作用下， 反应 12.0h， 以1 mg的产率得到marinomycin C deca-acetate
  参考文献：
  名称：

  Marinomycins A−D, Antitumor-Antibiotics of a New Structure Class from a Marine Actinomycete of the Recently Discovered Genus “Marinispora”

  摘要：

  Four antitumor-antibiotics of a new structure class, the marinomycins A-D (1-4), were isolated from the saline culture of a new group of marine actinomycetes, for which we have proposed the name "Marinispora". The structures of the marinomycins, which are unusual macrodiolides composed of dimeric 2-hydroxy-6-alkenyl-benzoic acid lactones with conjugated tetraene-pentahydroxy polyketide chains, were assigned by combined spectral and chemical methods. In room light, marinomycin A slowly isomerizes to its geometrical isomers marinomycins B and C. Marinomycins A-D show significant antimicrobial activities against drug resistant bacterial pathogens and demonstrate impressive and selective cancer cell cytotoxicities against six of the eight melanoma cell lines in the National Cancer Institute's 60 cell line panel. The discovery of these new compounds from a new, chemically rich genus further documents that marine actinomycetes are a significant resource for drug discovery.

  DOI：

  10.1021/ja0558948
• 作为产物：
  描述：

  5-ethynyl-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 在 双(乙腈)氯化钯(II) 2,6-二甲基吡啶 、 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 Schwartz's reagent 、 magnesium(II) perchlorate 、 KARSTEDT催化剂 、 四丁基氟化铵 、 potassium carbonate 、 三苯基膦 、 2,8,9-三异丁基-2,5,8,9-四氮杂-1-磷酸双向环[3.3.3]十一烷 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 115.66h， 生成 marinomycin C
  参考文献：
  名称：

  Marinomycins A-C 及其单体对应物 Monomarinomycin A 和iso-Monomarinomycin A 的全合成

  摘要：

  Marinomycins AC (1-3) 及其单体类似物 monomarinomycin A (m-1) 和 iso-monomarinomycin A (m-2)，是通过聚合策略从关键结构单元酮膦酸酯 5、醛 6 和二烯溴化羧基合成的酸 7. 首次尝试通过硼酸二烯基溴 4 的直接铃木型二聚/环化来构建海藻霉素 A [1，可通过光转化为海藻霉素 B (2) 和 C (3)]，导致过早闭环，在全局脱甲硅烷基化后，monomarinomycin A (m-1) 和 iso-monomarinomycin A (m-2) 收率良好，并且只有少量 (< 或 = 2%) 的所需产物。随后基于 Suzuki 型偶联的逐步方法显着提高了海藻霉素 A (1) 的总产率，从而显着提高了海藻霉素 B (2) 和 C (3) 的总产率。

  DOI：

  10.1021/ja068053p

文献信息

• Total Synthesis of Marinomycins A−C and of Their Monomeric Counterparts Monomarinomycin A and <i>iso</i>-Monomarinomycin A
  作者：K. C. Nicolaou、Andrea L. Nold、Robert R. Milburn、Corinna S. Schindler、Kevin P. Cole、Junichiro Yamaguchi

  DOI：10.1021/ja068053p

  日期：2007.2.1

  Marinomycins A-C (1-3), and their monomeric analogues monomarinomycin A (m-1) and iso-monomarinomycin A (m-2), were synthesized by a convergent strategy from key building blocks ketophosphonate 5, aldehyde 6, and dienyl bromide carboxylic acid 7. The first attempt to construct marinomycin A [1, convertible to marinomycins B (2) and C (3) by light] by direct Suzuki-type dimerization/cyclization of boronic

  Marinomycins AC (1-3) 及其单体类似物 monomarinomycin A (m-1) 和 iso-monomarinomycin A (m-2)，是通过聚合策略从关键结构单元酮膦酸酯 5、醛 6 和二烯溴化羧基合成的酸 7. 首次尝试通过硼酸二烯基溴 4 的直接铃木型二聚/环化来构建海藻霉素 A [1，可通过光转化为海藻霉素 B (2) 和 C (3)]，导致过早闭环，在全局脱甲硅烷基化后，monomarinomycin A (m-1) 和 iso-monomarinomycin A (m-2) 收率良好，并且只有少量 (< 或 = 2%) 的所需产物。随后基于 Suzuki 型偶联的逐步方法显着提高了海藻霉素 A (1) 的总产率，从而显着提高了海藻霉素 B (2) 和 C (3) 的总产率。
• Marinomycins A−D, Antitumor-Antibiotics of a New Structure Class from a Marine Actinomycete of the Recently Discovered Genus “<i>Marinispora</i>”
  作者：Hak Cheol Kwon、Christopher A. Kauffman、Paul R. Jensen、William Fenical

  DOI：10.1021/ja0558948

  日期：2006.2.1

  Four antitumor-antibiotics of a new structure class, the marinomycins A-D (1-4), were isolated from the saline culture of a new group of marine actinomycetes, for which we have proposed the name "Marinispora". The structures of the marinomycins, which are unusual macrodiolides composed of dimeric 2-hydroxy-6-alkenyl-benzoic acid lactones with conjugated tetraene-pentahydroxy polyketide chains, were assigned by combined spectral and chemical methods. In room light, marinomycin A slowly isomerizes to its geometrical isomers marinomycins B and C. Marinomycins A-D show significant antimicrobial activities against drug resistant bacterial pathogens and demonstrate impressive and selective cancer cell cytotoxicities against six of the eight melanoma cell lines in the National Cancer Institute's 60 cell line panel. The discovery of these new compounds from a new, chemically rich genus further documents that marine actinomycetes are a significant resource for drug discovery.