4-(甲硫基)-3-丁烯基异硫氰酸酯 | 51598-96-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 异硫氰酸盐
• 中文名称: 4-(甲硫基)-3-丁烯基异硫氰酸酯
• 英文名称: 4-methylsulfanyl-3-butenyl isothiocyanate
• 英文别名: 4-isothiocyanato-1-(methylthio)-1-butene；4-(methylthio)-3-butenyl isothiocyanate；4-(methylthio)-3-butenylisothiocyanate；4-methylthio-3-butenyl isothiocyanate；4-methylthio-3-butenylisothiocyanate；raphasatin；4-isothiocyanato-1-methylsulfanylbut-1-ene
• CAS: 51598-96-0
• 化学式: C₆H₉NS₂
• 分子量: 159.276
• InChiKey: RYSPJKHYSHFYEB-UHFFFAOYSA-N

物化性质

• 沸点：
  255.3±33.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  4-(甲硫基)-3-丁烯基异硫氰酸酯 在 双氧水 作用下， 以 甲醇 为溶剂， 生成 莱菔素
  参考文献：
  名称：

  Cytotoxic and Antioxidant Activity of 4-Methylthio-3-butenyl Isothiocyanate from Raphanus sativus L. (Kaiware Daikon) Sprouts

  摘要：

  There is high current interest in the chemopreventive potential of Brassica vegetables (cruciferae), particularly due to their content in glucosinolates (GL), which upon myrosinase hydrolysis, release the corresponding isythiocyanates (ITC). Some ITCs, such as sulforaphane (SFN) from broccoli (Brassica oleacea italica), have been found to possess anticancer activity through induction of apoptosis in selected cell lines, as well as indirect antioxidant activity through induction of phase 11 detoxifying enzymes. Japanese daikon (Raphanus sativus L.) is possibly the vegetable with the highest per capita consumption within the Brassicaceae family. Thanks to a recently improved gram scale production process, it was possible to prepare sufficient amounts of the GL glucoraphasatin (GRH) as well as the corresponding ITC 4-methylthio-3-butenyl isothiocyanate (GRH-ITC) from its sprouts. This paper reports a study on the cytotoxic and apoptotic activities of GRH-ITC compared with the oxidized counterpart 4-methylsulfinyl-3-butenyl isothiocyanate (GRE-ITC) on three human colon carcinoma cell lines (LoVo, HCT-116, and HT-29) together with a detailed kinetic investigation of the direct antioxidant/radical scavenging ability of GRH and GRH-ITC. Both GRH-ITC and GRE-ITC reduced cell proliferation in a dose-dependent manner and induced apoptosis in the three cancer cell lines. The compounds significantly (p < 0 05) increased Bax and decreased Bcl2 protein expression, as well as producing caspase-9 and PARP-1 cleavage after 3 days of exposure in the three cancer cell lines. GRH-ITC treatment was shown to have no toxicity with regard to normal human lymphocytes (-15 +/- 5%) in comparison with SFN (complete growth inhibition). GRH and GRH-ITC were able to quench the 2,2-diphenyl-1-picrylhydrazyl radical, with second-order rate constants of 14.0 +/- 2.8 and 43.1 +/- 9.5 M-1 s(-1), respectively (at 298 K in methanol), whereas the corresponding value measured here for the reference antioxidant alpha-tocopherol was 425 +/- 40 M-1 s(-1). GRH reacted with H2O2 and tert-butyl hydroperoxide in water (pH 7.4) at 37 degrees C, with rate constants of 1.9 +/- 0.3 x 10(-2) and 9.5 +/- 0.3 x 10(-4) M-1 s(-1) (paralleling recently developed synthetic antioxidants) being quantitatively (>97%) converted to GRE. It is demonstrated that GRH-ITC has interesting antioxidant/radical scavenging properties, associated with a selective cylotoxic/apoptotic activity toward three human colon carcinoma cell lines, and very limited toxicity on normal human T-lymphocytes.

  DOI：

  10.1021/jf073123c
• 作为产物：
  描述：

  4-methylsulfanyl-3-butenyl glucosinolate 以 aq. phosphate buffer 为溶剂， 生成 4-(甲硫基)-3-丁烯基异硫氰酸酯
  参考文献：
  名称：

  Induction of Apoptosis and Cytotoxicity by Raphasatin in Human Breast Adenocarcinoma MCF-7 Cells

  摘要：

  葡萄萄糖芥子苷（GRH）是一种存在于十字花科植物中丰富的硫代葡萄糖苷，被肌醇酶水解成为芥子烷，被认为是其抗癌活性的原因；然而，其作用机制尚未研究，特别是在人类细胞系中。本研究的目的是确定芥子烷的细胞毒性，并评估其在人类乳腺腺癌MCF-7细胞中引起凋亡和调节细胞周期阻滞的潜力。通过将细胞与葡萄糖芥子苷或芥子烷（0-100 µM）孵育24、48和72小时来确定细胞毒性。GRH通过3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四氮唑溴化物（MTT）试验未表现出细胞毒性。当肌醇酶被加入孵育系统中将GRH转化为芥子烷时，细胞毒性明显。将细胞暴露于芥子烷刺激凋亡，如细胞萎缩、膜泡、染色质浓缩和核碎片化。此外，使用Annexin V-FITC试验，芥子烷诱导凋亡，随着不同阶段的细胞分布发生变化；此外，芥子烷还导致MCF-7细胞在G2 + M期阻滞。总之，芥子烷通过诱导凋亡和细胞周期阻滞，在人类乳腺腺癌（MCF-7）细胞中展示了抗癌潜力。

  DOI：

  10.3390/molecules23123092

文献信息

• Formation of raphanusanins depends on extraction procedure and solvent
  作者：Hiroki Matsuoka、Yoshinori Toda、Koichi Yoneyama、Yasushi Uda

  DOI：10.1016/s0031-9422(98)80056-3

  日期：1998.3

  3-[α-methoxy-(α-methylthio)methyl]-2-thioxopyrrolidine, which had been reported as a light-induced plant growth inhibitor in roots and seedlings of radish, was examined using different extraction procedures and solvents including methanol- d 4 . Both (3 R *,6 R *)- and (3 R *,6 S *)-isomers of the compound were detected in the methanol extract of autolysed radish roots, but not in the acetone nor in

  摘要 萝卜硫素 3-[α-甲氧基-(α-甲硫基)甲基]-2-硫代吡咯烷是萝卜根和幼苗中的光诱导植物生长抑制剂，使用不同的提取方法和溶剂包括甲醇-d 4 。在自溶萝卜根的甲醇提取物中检测到该化合物的 (3 R *,6 R *)- 和 (3 R *,6 S *)-异构体，但在丙酮和水提取物中均未检测到。当用甲醇-d 4 提取自溶萝卜幼苗时，形成具有CD 3 基团的萝卜花素-d 3 代替萝卜花素。在漂白的幼苗和根的情况下，仅在黑芥子酶处理的匀浆的甲醇提取物中检测到萝卜苷。这些结果表明 raphantin 或 raphanusanin 是在用甲醇提取萝卜过程中形成的人工产物，
• XPO1蛋白抑制剂
  申请人：领思科技(大连)有限公司

  公开号：CN104725291B

  公开（公告）日：2017-06-16

  本发明公开一类XPO1蛋白抑制剂，具有通式F的结构。本发明所述的XPO1蛋白抑制剂在水中的溶解度非常好，以莱菔素为代表，该类化合物对XPO1蛋白的抑制活性极高，并且副作用极小，生物安全度和生物利用度好，非常适合于临床应用，因此具有巨大的潜在的市场空间和经济效益。
• Antimutagenic Properties of 3,5-Disubstituted 2-Thiohydantoins
  作者：Asaka Takahashi、Hiroki Matsuoka、Yoshio Ozawa、Yasushi Uda

  DOI：10.1021/jf980430x

  日期：1998.12.1

  3,5-Disubstituted 2-thiohydantoins, which were prepared:by the reaction of allyl isothiocyanate (AITC) or 4-(methylthio)-3-butenyl isothiocyanate (MTBI) with various amino acids, were assayed for their inhibitory effects on the mutagenicity of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) on Salmonella typhimurium TA 98. When the 3,5-disubstituted 2-thiohydantoins (125-500 mu g/mL) were simultaneously preincubated with the bacterial strain, IQ (0.5 mu g/mL), and rat microsomal fraction (S9 mix) for 20 min, a dose-dependent inhibition of IQ mutagenicity was observed in the tested compounds except one prepared from MTBI and L-methionine. This inhibition ranged from 23% to 86%. The inhibitory effect either disappeared or was largely reduced to 5-19%, when the 3,5-disubstituted 2-thiohydantoins were added after metabolic activation of IQ with S9 mix. These results suggest that the 3,5-disubstituted 2-thiohydantoins probably acted as an inhibitor of the S9 mix-mediated metabolic activation of the mutagen.
• Matsuoka, Hiroki; Toda, Yoshinori; Yanagi, Kenji, Bioscience, Biotechnology and Biochemistry, 1997, vol. 61, # 12, p. 2109 - 2112
  作者：Matsuoka, Hiroki、Toda, Yoshinori、Yanagi, Kenji、Takahashi, Asaka、Yoneyama, Koichi、Uda, Yasushi

  DOI：——

  日期：——
• Thermal Degradation of Sulforaphane in Aqueous Solution
  作者：Yi Jin、Mingfu Wang、Robert T. Rosen、Chi-Tang Ho

  DOI：10.1021/jf990082e

  日期：1999.8.1

  Sulforaphane, a cancer chemopreventive agent identified from broccoli, was degraded in an aqueous solution at 50 and 100 degrees C. The reaction mixtures were extracted with methylene chloride and analyzed by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). Dimethyl disulfide, S-methyl methylthiosulfinate, S-methyl methylthiosulfonate, methyl (methylthio)methyl disulfide, 1,2,4-trithiolane, 4-isothiocyanato-1-(methylthio)-1-butene and 3-butenyl isothiocyanate were identified as volatile decomposition products. After methylene chloride extraction, the aqueous layer was dried and silica gel column chromatography was used to separate and purify the nonvolatile decomposition products. The major thermal degradation compound was determined by H-1 NMR, C-13 NMR, and FAB-MS as N,N'-di(4-methylsulfinyl)butyl thiourea. A possible mechanism for the formation of these products is proposed.'''.