basiliskamide A

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: basiliskamide A
• 英文别名: [(3R,4S,5R,6R,8E,10Z)-12-amino-6-hydroxy-3,5-dimethyl-12-oxododeca-8,10-dien-4-yl] (E)-3-phenylprop-2-enoate
• 化学式: C₂₃H₃₁NO₄
• 分子量: 385.503
• InChiKey: QAHZDGAHECEVRM-HXKCHMFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  basiliskamide A 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 18.0h， 以64%的产率得到(2Z,4E)-(7R,8R,9S,10R)-7,9-Dihydroxy-8,10-dimethyl-dodeca-2,4-dienoic acid amide
  参考文献：
  名称：

  Tupuseleiamides and Basiliskamides, New Acyldipeptides and Antifungal Polyketides Produced in Culture by a Bacillus laterosporus Isolate Obtained from a Tropical Marine Habitat

  摘要：

  Laboratory cultures of PNG 276, a Bacillus laterosporus isolate obtained from coastal waters off Papua New Guinea, have been shown to produce the novel metabolites basiliskamide A (1), basiliskamide B (2), tupuseleiamide A (3), and tupusleiamide B (4). The structures of I to 4 were elucidated by analysis of spectroscopic data and chemical degradation. Basiliskamides A (1) and B (g) show potent in vitro anti-Candida, activity.

  DOI：

  10.1021/np0201321

文献信息

• Antifungal and antimycobacterial basiliskamides
  申请人：Kelly T. Michael

  公开号：US20050277779A1

  公开（公告）日：2005-12-15

  Antibiotic polyketide compounds are provided having the formula wherein: R 1 and R 2 are the same or different and are independently H or R; R is a structural fragment having a saturated or unsaturated linear, branched, or cyclic, skeleton containing one to ten carbon atoms in which the carbon atoms may be optionally substituted with a substituent selected from the group consisting of: —OH; ═O; —OR 5 ; —O 2 CR 5 , —SH; —SR 5 ; —SOCR 5 ; —NH 2 ; —NH 5 ; —NH(R 5 ) 2 ; —NHCOR 5 ; NRCOR 5 ; —I; —Br; —Cl; —F; —CN; —CO 2 H; —CO 2 R 5 ; —CH0; —COR 5 ; —CONH 2 ; —CONHR 5 ; —CON(R 5 ) 2 ; —COSH; —COSR 5 ; —N0 2 ; —S0 3 H; —SOR 5 ; and —SO 2 R 5 , wherein R 5 is a linear, branched or cyclic, one to ten carbon saturated or unsaturated alkyl group; R 3 and R 4 are different and are independently selected from the groups consisting of OH, wherein Z 1 and Z are linear or branched saturated or unsaturated, one to en carbon fragments optionally substituted with Y; Ar is a monocyclic, bicyclic or tricyclic, fully or partially aromatic system containing five or six membered carbocyclic or, oxygen, nitrogen or sulphur containing heterocyclic rings, optionally substituted with R or Y; Y is selected from the group consisting of: H; ═O, —OH; —OR; —0 2 CR; —SH; —SR; —SOCR; —NH 2 ; —NHR; —NH(R) 2 ; —NHCOR; NRCOR; —I; —Br; —Cl; —F; —CN— —CO 2 H; —CO 2 R; —CHO; —COR; —CONH 2 ; —CONHR: —CON(R) 2 ; —COSH; —COSR; —N0 2 ; —SO 3 H; —SOR; —SO 2 R; and, —O— (epoxide); W is H or R; with the provisos that when W is H, R 2 is not H; when R 2 is CH 3 , W is not n-propyl; and, one of R 3 and R 4 is (a) or (b) and another of R 3 and R 4 is OH.

  提供了具有以下式子的抗生素多酮化合物： 其中： R1和R2相同或不同，且独立地为H或R； R是具有饱和或不饱和的线性、支链或环状骨架的结构片段，其中含有一到十个碳原子，该碳原子可以选择性地被取代为来自以下群组的取代基：—OH；═O；—OR5；—O2CR5；—SH；—SR5；—SOCR5；—NH2；—NH5；—NH(R5)2；—NHCOR5；NRCOR5；—I；—Br；—Cl；—F；—CN；—CO2H；—CO2R5；—CH0；—COR5；—CONH2；—CONHR5；—CON(R5)2；—COSH；—COSR5；—N02；—S03H；—SOR5；和—SO2R5，其中R5是一条线性、支链或环状、饱和或不饱和的十个碳原子以下的烷基； R3和R4不同，且独立地从以下群组中选择：OH，其中Z1和Z是线性或支链、饱和或不饱和的一到十个碳原子片段，可以选择性地被Y取代； Ar是一个单环、双环或三环的、完全或部分芳香的系统，其中包含五个或六个成员的碳环或含氧、氮或硫的杂环，可以选择性地被R或Y取代； Y从以下群组中选择：H；═O；—OH；—OR；—02CR；—SH；—SR；—SOCR；—NH2；—NHR；—NH(R)2；—NHCOR；NRCOR；—I；—Br；—Cl；—F；—CN；—CO2H；—CO2R；—CHO；—COR；—CONH2；—CONHR；—CON(R)2；—COSH；—COSR；—N02；—SO3H；—SOR；—SO2R；和—O—（环氧）； W为H或R； 但是，当W为H时，R2不为H；当R2为CH3时，W不为n-丙基；并且，R3和R4中的一个为（a）或（b），另一个为OH。

表征谱图