(2S,3S)-3,4-环氧-2-(3-甲氧基-5-甲基-1-萘氧基)-3-甲基丁酰胺 | 110450-52-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: (2S,3S)-3,4-环氧-2-(3-甲氧基-5-甲基-1-萘氧基)-3-甲基丁酰胺
• 英文名称: (2S,3S)-3,4-epoxy-2-(3-methoxy-5-methyl-1-naphthoyloxy)-3-methylbutanamide
• 英文别名: (2S,4-Epoxy-2-(3-methoxy-5-methyl-1-naphthoyloxy)-3-methylbutanamide；[(1S)-2-amino-1-[(2S)-2-methyloxiran-2-yl]-2-oxoethyl] 3-methoxy-5-methylnaphthalene-1-carboxylate
• CAS: 110450-52-7
• 化学式: C₁₈H₁₉NO₅
• 分子量: 329.353
• InChiKey: KDYGKLQSWCCUFT-QAPCUYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  91.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3,4-环氧-2-(3-甲氧基-5-甲基-1-萘氧基)-3-甲基丁酰胺 以50%的产率得到
  参考文献：
  名称：

  SHIBUYA, MASAYUKI;TERAUCHI, HIDEO, TETRAHEDRON LETT., 28,(1987) N 23, 2619-2622

  摘要：

  DOI：
• 作为产物：
  描述：

  3,3-二甲基丙烯酸 在 10% palladium on active carbon 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 氢氧化钾 、 ammonium hydroxide 、 AD-mix-α 、 bis(acetylacetonate)oxovanadium 、 甲基磺酰胺 、 camphor-10-sulfonic acid 、 四丁基溴化铵 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 碳酸氢钠 、 sodium carbonate 、 1-羟基苯并三唑 、 三乙胺 作用下， 以 甲醇 、 癸烷 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 反应 175.0h， 生成 (2S,3S)-3,4-环氧-2-(3-甲氧基-5-甲基-1-萘氧基)-3-甲基丁酰胺
  参考文献：
  名称：

  Bryant, Helen J.; Dardonville, Christophe Y.; Hodgkinson, Timothy J., Journal of the Chemical Society. Perkin transactions I, 1998, # 7, p. 1249 - 1255

  摘要：

  DOI：

文献信息

• Synthetic studies of carzinophilin. Part 1: Synthesis of 2-methylidene-1-azabicyclo[3.1.0]hexane systems related to carzinophilin
  作者：Masaru Hashimoto、Miyoko Matsumoto、Shiro Terashima

  DOI：10.1016/s0040-4020(03)00377-6

  日期：2003.4

  Synthesis of the model compounds of carzinophilin carrying 2-methylidene-1-aza-bicyclo[3.1.0]hexane systems was achieved. Formation of malonylidenes or N-acyl-glycinylidenepyrrolidines was carried out by utilizing Eschenmoser's sulfide contraction or Herdeis's condensation between the 2-methylthio-Δ1-pyrrolone derivatives and ethyl nitroacetate, respectively. The 1-azabicyclo-[3.1.0]hexane systems

  合成了带有2-亚甲基-1-氮杂-双环[3.1.0]己烷体系的卡那菲林模型化合物。malonylidenes或形成ñ酰基-glycinylidenepyrrolidines通过利用Eschenmoser的硫化物的收缩或Herdeis的2-甲硫-Δ之间的缩合进行1个分别-pyrrolone衍生物和硝基乙酸乙酯。1-氮杂双环-[3.1.0]己烷体系是通过碱促进的氮丙啶形成而构建的。
• Synthetic studies toward azinomycins A and B. Synthesis and absolute stereochemistry of the minor component isolated from azinomycins producing strain
  作者：Masayuki Shibuya、Hideo Terauchi

  DOI：10.1016/s0040-4039(00)96163-x

  日期：1987.1

  The minor component isolated from Streptomyces griseofuscus S42227 was synthesized in optically active form and the absolute configurations of C-18 and C-19 of azinomycins were presumed as 18S, 19S.

  分离自灰链霉菌S42227的次要成分以光学活性形式合成，并且阿奇霉素的C-18和C-19的绝对构型假定为18S，19S。
• Synthetic studies of carzinophilin. Part 4: Chemical and biological properties of carzinophilin analogues
  作者：Masaru Hashimoto、Miyoko Matsumoto、Kaoru Yamada、Shiro Terashima

  DOI：10.1016/s0040-4020(03)00380-6

  日期：2003.4

  Chemical and biological properties of carzinophilin congeners obtained in the course of our synthetic studies were investigated. These studies revealed feasibility for the use of some analogues as a double alkylating agent. Further, analogues carrying the naphthalene and the epoxide parts were found to show remarkable in vitro cytotoxicity and in vivo antitumor activity. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis of Functional “Top-Half” Partial Structures of Azinomycin A and B
  作者：Robert S. Coleman、Mark T. Tierney、Sarah B. Cortright、Daniel J. Carper

  DOI：10.1021/jo7014888

  日期：2007.9.1

  [GRAPHICS]The design and synthesis of a detailed series of functional "top-half" substructures of azinomycin A and B is described.
• Studies on the Mechanism of Action of Azinomycin B:  Definition of Regioselectivity and Sequence Selectivity of DNA Cross-Link Formation and Clarification of the Role of the Naphthoate
  作者：Robert S. Coleman、Ronelito J. Perez、Christopher H. Burk、Antonio Navarro

  DOI：10.1021/ja025563k

  日期：2002.11.1

  Evaluation of the sequence selectivity, noncovalent association, and orientation of the DNA cross-linking agent azinomycin B on its duplex DNA receptor is described. A strong correlation between sequence nucleophilicity and cross-linking yield was observed, and steric effects due to the thymine C5-methyl group were identified. Detailed studies on the role of the azinomycin naphthoate using viscometry, fluorescence contact energy transfer, and DNA unwinding assays point to a nonintercalative binding mode for this group. A kinetic assay for agent regioselectivity was used to determine the orientation of binding and covalent cross-link formation.