pericoxide

• 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: pericoxide
• 英文别名: methyl (1R,4S,5S,6S)-4,5-dihydroxy-7-oxabicyclo[4.1.0]hept-2-ene-2-carboxylate
• 化学式: C₈H₁₀O₅
• 分子量: 186.164
• InChiKey: CHSQMUXGDINCHS-YTLHQDLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  79.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  pericoxide 在 水 、 copper(II) sulfate 、 三乙胺 、 sodium chloride 、 锌 作用下， 以 甲醇 、 水 为溶剂， 生成 甲基(3S,4S,5S,6S)-3,4,5-三羟基-6-甲氧基-1-环己烯-1-羧酸酯
  参考文献：
  名称：

  [EN] SHIKIMATE ANALOGUES AND METHODS OF USE
  [FR] ANALOGUES DE SHIKIMATE ET MÉTHODES D'UTILISATION

  摘要：

  本公开至少在某些实施例中涉及植酸（香草酸）类似物及其组成物，包含植酸类似物或其组成物的工具包，以及用于处理上皮表面在暴露于刺激物、过敏原和毒性剂（例如漆油）之前或之后的化合物和组成物的使用方法。

  公开号：

  WO2017142866A1
• 作为产物：
  描述：

  (+)-6-bromopericosine A 在 正丁基锂 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 pericoxide
  参考文献：
  名称：

  6-卤素取代的 Pericosine A 的合成及其抗肿瘤和抗糖苷酶活性的评价

  摘要：

  合成了 6-氟、6-溴和 6-碘哌啶 A 的对映异构体。还开发了一种通过 6-溴哌啶 A 有效合成过氧化物的两种对映异构体的方法。这些 6 卤代取代的 pericosine A 衍生物根据它们对三种类型的肿瘤细胞（p388、L1210 和 HL-60）的抗肿瘤活性和糖苷酶抑制活性进行了评估。溴和碘同系物对所研究的三种肿瘤细胞系表现出与 pericosine A 相似的中等抗肿瘤活性。氟化化合物的活性低于其他化合物，包括 pericosine A。在抗肿瘤试验中，没有观察到任何卤化化合物的对映异构体之间的效力有显着差异。同时，

  DOI：

  10.3390/md20070438

文献信息

• Reactivity studies in the shikimic acid series
  作者：Stephen Bowles、Malcolm M. Campbell、Malcolm Sainsbury、Gareth M. Davies

  DOI：10.1016/s0040-4039(01)80490-1

  日期：1989.1

  6α-fluoroshikimate from the acetonide of methyl 3,4-dihydro-3α,4α-cyclohexenoate is described. This work has importance for the preparation of 6-substituted shikimic acid derivatives useful in the study of the biosynthesis of aromatic amino acids via the shikimic acid pathway.

  已经研究了3，4-二氢苯甲酸甲酯的区域和立体选择性环氧化，并且描述了由3，4-二氢-3α，4α-环己酸甲酯的丙酮化物合成外消旋6α-氟代草酸甲酯。这项工作对于制备6-取代的iki草酸衍生物具有重要意义，该衍生物可用于通过sh草酸途径生物合成芳族氨基酸。
• Reactivity studies in the shikimic acid series: The synthesis of racemic methyl 6α-fluoroshikimate
  作者：Stephen A. Bowles、Malcolm M. Campbell、Malcolm Sainsbury、Gareth M. Davies

  DOI：10.1016/s0040-4020(01)90533-2

  日期：1990.1

  The regio- and stereo-selective epoxidation of methyl 3,4-dihydrobenzoate derivatives has been investigated. Perbenzimidic acid leads only to epoxides formed at the Δ1,2 bond. More electrophilic reagents such as MCPBA also give products of this type, as well as epoxides formed through attack at the Δ5,6 bond. Reactions of the 3,4-dihydrobenzoates with thiophenate anion have been undertaken as a means

  已经研究了3，4-二氢苯甲酸甲酯衍生物的区域和立体选择性环氧化。Perbenzimidic酸仅导致在Δ形成环氧化物1,2-键。更多的亲电试剂（例如MCPBA）也可以提供这种类型的产物，以及通过攻击Δ5,6键形成的环氧化物。3,4- dihydrobenzoates与thiophenate阴离子的反应已经进行作为保护Δ的手段1,2-键，并由此控制环氧化的区域选择性。通过3，4-二氢-3，4-异丙基二烯二氧基苯甲酸甲酯的环氧化物的开环，已经实现了外消旋6α-氟代草酸甲酯的合成。
• An Electrophilic Natural Product Provides a Safe and Robust Odor Neutralization Approach To Counteract Malodorous Organosulfur Metabolites Encountered in Skunk Spray
  作者：Lin Du、Charissa Munteanu、Jarrod B. King、Doug E. Frantz、Robert H. Cichewicz

  DOI：10.1021/acs.jnatprod.9b00415

  日期：2019.7.26

  The anal secretions of skunks comprise several types of malodorous organosulfur compounds. The pungent metabolites are used defensively by skunks to repel threats posed by predators, and in many parts of the world, those perceived threats include humans and their pets. The extremely low thresholds for detection of the organosulfur metabolites make efforts to "de-skunk" people, animals, and clothing a process fraught with many challenges. The fungal-derived metabolite pericosine A (4) is a promiscuous yet stabile electrophilic compound that we propose is used by some fungi as a novel form of chemical defense. Our investigations have indicated that pericosine A readily reacts with skunk-spray secretions to transform them into odorless products. Mechanistic and computational studies suggested that pericosine A and its synthetic analogues react via S_N2'-type mechanisms with thiols and thioacetates under aqueous conditions to generate stable thioethers. Testing revealed that pericosine A did not cause skin or eye irritation and was highly effective at deodorizing skunk anal gland secretions when formulated to include adjunctive cosmetic ingredients.
• SHIKIMATE ANALOGUES AND METHODS OF USE
  申请人：The Board of Regents of the University of Oklahoma

  公开号：US20190038579A1

  公开（公告）日：2019-02-07

  The present disclosure, in at least certain embodiments, is directed to shikimate (shikimic acid) analogues and compositions thereof, kits which contain the shikimate analogues or compositions thereof, and methods of use of the compounds and compositions for treating epithelial surfaces before or following exposure to irritants, allergens, and toxic agents (for example, urushiol).
• [EN] SHIKIMATE ANALOGUES AND METHODS OF USE<br/>[FR] ANALOGUES DE SHIKIMATE ET MÉTHODES D'UTILISATION
  申请人：UNIV OKLAHOMA

  公开号：WO2017142866A1

  公开（公告）日：2017-08-24

  The present disclosure, in at least certain embodiments, is directed to shikimate (shikimic acid) analogues and compositions thereof, kits which contain the shikimate analogues or compositions thereof, and methods of use of the compounds and compositions for treating epithelial surfaces before or following exposure to irritants, allergens, and toxic agents (for example, urushiol).

  本公开至少在某些实施例中涉及植酸（香草酸）类似物及其组成物，包含植酸类似物或其组成物的工具包，以及用于处理上皮表面在暴露于刺激物、过敏原和毒性剂（例如漆油）之前或之后的化合物和组成物的使用方法。