cis-arctigenin | 81446-30-2

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: cis-arctigenin
• 英文别名: (3S,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
• CAS: 81446-30-2
• 化学式: C₂₁H₂₄O₆
• 分子量: 372.418
• InChiKey: NQWVSMVXKMHKTF-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  cis-arctigenin 在 氢氧化钾 作用下， 生成 (+)-arctigenin
  参考文献：
  名称：

  Prestegane A, from Steganotaenia araliacea Hochst,: The First Natural Dibenzylbutanolide Lignan with a meta-Phenol - a short synthesis of cis and trans (±) Arctigenin -

  摘要：

  DOI：

  10.1016/s0040-4039(00)88144-7
• 作为产物：
  描述：

  (R)-3-Cyano-2-<(3,4-dimethoxyphenyl)methyl>propyl acetate 在 palladium on activated charcoal 盐酸 、 lithium hydroxide 、 sodium hydroxide 、 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 水 、 乙酸乙酯 为溶剂， 生成 cis-arctigenin
  参考文献：
  名称：

  Synthesis and anti-HIV activity of dibenzylbutyrolactone lignans

  摘要：

  DOI：

  10.1016/0960-894x(96)00158-8

文献信息

• Catalytic asymmetric synthesis of (−)-arctigenin using a chiral Ir complex
  作者：Rui Jiang、Da-Yang Zhou、Kaori Asano、Takayoshi Suzuki、Takeyuki Suzuki

  DOI：10.1016/j.tet.2023.133287

  日期：2023.3

  The catalytic asymmetric synthesis of (−)-arctigenin is reported. The central optically pure lactone intermediate is obtained either from an Ir-catalyzed asymmetric Tishchenko reaction or an asymmetric oxidative lactonization and subsequently converted to β-iodomethyl-α-methylene-γ-butyrolactone. Several recent Negishi coupling protocols were investigated for the introduction of an aryl unit in the

  报道了 (−)-arctigenin 的催化不对称合成。中心光学纯内酯中间体是从 Ir 催化的不对称 Tishchenko 反应或不对称氧化内酯化反应中获得的，随后转化为 β-碘甲基-α-亚甲基-γ-丁内酯。为了在 α-亚甲基-γ-丁内酯存在下引入芳基单元，研究了几个最近的 Negishi 偶联方案。在无保护基的条件下，使用非对映选择性 Rh 催化的共轭加成和质子化实现了第二个芳基单元的引入。
• Discovery of stereospecific cytotoxicity of (8R,8′R)-trans-arctigenin against insect cells and structure-activity relationship on aromatic ring
  作者：Satoshi Yamauchi、Asuka Nishimoto、Hisashi Nishiwaki、Kosuke Nishi、Takuya Sugahara

  DOI：10.1016/j.bmcl.2020.127191

  日期：2020.7

  One of the arctigenin stereoisomers, (8R,8'R)-trans-form 1, showed stereospecific cytotoxicity against insect cells, Sf9 and NIAS-AeAl-2 cells. By the comparison with other stereoisomers, the most importance of the 8'R stereochemistry for the higher activities was clarified. On the other hand, the wider range of activity level among stereoisomers against cancer cells, HL-60, was not observed. The structure-activity relationship research using derivatives bearing (8R,8'R)-trans-form was performed to show the same level of activities of 3-iodo, 4-iodo, and 3,4-methylenedioxy derivatives 28, 29, and 36 as (8R,8'R)-trans-arctigenin 1. In the examination of thiono derivatives, 4-iodo thiono and 3,4-methylenedioxy thiono derivatives 66, 67 showed similar level of activities to that of (8R,8'R)-trans-arctigenin 1. The expression of ribosomal 28S rRNA gene of Sf9 cells was increased by (8R,8'R)-trans-arctigenin 1, whereas a degradation of DNA was not observed.
• Evaluation of Pulse-polio immunisation in rural area of Maharashtra
  作者：S. V. Chincholikar、R. D. Prayag

  DOI：10.1007/bf02762174

  日期：2000.9

  An evaluation survey on Pulse-polio Immunisation (PPI) in January 2000 was carried out in rural areas of Maharashtra to assess the immunisation coverage, the knowledge regarding pulse-polio and the routine immunisation schedule. House-to-house survey was carried out and information was collected by interviewing the parents of 778 children. It was observed that PPI coverage was excellent i.e., 98%. Majority of informants were female. Knowledge about pulse-polio had a direct relationship with literacy. But knowledge regarding routine immunisation and the polio disease was not found satisfactory. Excellent coverage of pulse-polio Immunisation was found because of an organised and extensive campaign, use of mass media like T.V., radio, and home visits of peripheral health staff (as told by the informants). The distance of approach to a polio booth was less than a kilometre in almost all cases. Behaviour of health staff was satisfactory everywhere. The time-period required for getting vaccinated after arrival at the polio booth was less than 5 minutes. Thus it was a worthwhile attempt to evaluate PPI coverage is rural areas of Maharasthra. Excellent coverage of pulse-polio immunisation gives us the picture that poliomyelitis is on the verge of being eradicated from India, if the excellent coverage of PPI is followed by effective surveillence.
• Nishibe, Sansei; Chiba, Mariko; Sakushima, Akiyo, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 3, p. 850 - 860
  作者：Nishibe, Sansei、Chiba, Mariko、Sakushima, Akiyo、Hisada, Sueo、Yamanouchi, Sakae、et al.

  DOI：——

  日期：——
• Ohmaki, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1935, vol. 55, p. 816,825, 826; dtsch. Ref. S. 159, 161
  作者：Ohmaki

  DOI：——

  日期：——