5-乙烯基-1,3-恶唑烷-2-硫酮 | 13190-34-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 5-乙烯基-1,3-恶唑烷-2-硫酮
• 英文名称: goitrin
• 英文别名: 5-vinyloxazolidine-2-thione；5-vinyl-1,3-oxazolidine-2-thione；(R,S)-goitrin；(R,S)-epigoitrin；DL-goitrin；5-ethenyl-1,3-oxazolidine-2-thione
• CAS: 13190-34-6；13997-13-2；500-12-9
• 化学式: C₅H₇NOS
• mdl: MFCD00015467
• 分子量: 129.183
• InChiKey: UZQVYLOFLQICCT-UHFFFAOYSA-N

物化性质

• 熔点：
  64-65°C
• 沸点：
  150.6±43.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜
• 颜色/状态：
  Large prisms from ether
• 稳定性/保质期：
  按规格使用和贮存，不会发生分解，避免与氧化物接触。
• 旋光度：
  Specific optical rotation at 31 °C for D (sodium) line = -70.5 deg (c=2 in methanol).
• 解离常数：
  pKa = 10.5

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  2

ADMET

毒理性

• 相互作用

Goitrin是一种强效致甲状腺物质，已被证明能够诱导谷胱甘肽S-转移酶（GST）活性并增加黄曲霉毒素解毒。

Goitrin is a potent goitrogen that has been shown to induce glutathione S-transferase (GST) activity and to increase aflatoxin detoxification.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

goitrin --十字花科蔬菜和油菜中自然存在的化合物--可以通过用亚硝酸盐在胃部条件下处理轻松地进行亚硝化反应，失去硫后生成N-亚硝基恶唑烷酮4。这个产品在Ames沙门氏菌/哺乳动物微粒体测试中的致突变模式和能力与N-亚硝基-N-甲基-N'-硝基胍（MNNG）相似。

goitrin --a naturally occurring compound in cruciferous vegetables and rape--could be easily nitrosated by treatment with nitrite under stomach conditions, yielding with loss of sulfur the N-nitroso- oxazolidone 4. This product has a mutagenicity pattern and potency similar to that of N-nitroso-N-methyl-N'- nitroguanidine (MNNG) in the Ames Salmonella/mammalian microsome test.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

基本治疗：建立专利气道。如有必要，进行吸痰。观察呼吸不足的迹象，并在需要时辅助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，并在必要时进行治疗……。监测休克，并在必要时进行治疗……。预测并处理癫痫发作……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用生理盐水连续冲洗每只眼睛……。不要使用催吐剂。对于误食，如果患者能吞咽、有强烈的干呕反射且不流口水，则用水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释……。在去污后，用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

高级治疗：对于无意识、严重肺水肿或呼吸停止的患者，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊面罩装置的正压通气技术可能有益。监测心率和必要时治疗心律失常。 ... 开始静脉输液，使用D5W/SRP：“保持开放”，最低流量/。如果出现低血容量的迹象，使用乳酸钠林格氏液。注意液体过载的迹象。考虑使用药物治疗肺水肿。对于伴有低血容量迹象的低血压，谨慎给予液体。注意液体过载的迹象。用地西泮（安定）治疗癫痫。使用丙美卡因氢氯化物协助眼部冲洗。/毒药A和B/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

实验室动物：急性暴露/通过平行线分析评估了口服给予甘露素对雏鸡的拮抗甲状腺活性，使用了四个指标。甘露素在鸡体内的相对效力估计大约为PTU导致甲状腺肿大的0.31倍，对血浆甲状腺激素降低效果的0.06倍，以及对甲状腺激素生物合成抑制效果的0.08倍。可以得出结论，当口服给予甘露素时，雏鸡的甲状腺激素合成并没有像甲状腺肿大预期的那样受到明显的抑制。

/LABORATORY ANIMALS: Acute Exposure/ Antithyroid activity of orally administered goitrin was assessed by parallel-line assay in chicks using four indices. The relative potency of goitrin in chicks was estimated to be approximately 0.31 times the potency of PTU in causing enlargement of thyroid gland, 0.06 times in effect on depression in plasma thyroid hormone, and 0.08 times in inhibitory effects on biosynthesis of thyroid hormone in the gland. It might be concluded that thyroid hormone synthesis is not so much suppressed to the degree expected from the enlargement of thyroid gland when goitrin is administered orally to the chick.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

共六头牛，分成3组，在7天内分别喂食含有6克/千克硫代葡萄糖苷的菜籽饼，不同数量。这些牛每天挤奶两次...当菜籽饼按总饲料的0.39%，1.9%和3.9%分别喂食时，牛奶中的硫代葡萄糖苷含量分别为37、163和707微克/升。这些数值对应于饲料中原始前硫代葡萄糖苷含量的大约0.1%的转移。最后一次喂食菜籽饼后12小时，牛奶中的硫代葡萄糖苷含量低于7ppb的检测限。

A total of six cows, divided into 3 groups, were fed various amounts of rape cake containing 6 g of goitrin/kg over a period of 7 days. The cows were milked twice a day ... . When rape cake was fed at 0.39, 1.9 and 3.9% resp. of the total feed this resulted in medium goitrin values of 37, 163 and 707 ug/l milk. These values correspond to a transfer of about 0.1% of the original progoitrin content in the feed. 12 h after the last rape feeding the amount of goitrin in the milk was below the detection limit of 7 ppb.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 安全说明：
  S22
• WGK Germany：
  3

制备方法与用途

生物活性

去氧板蓝根苷（DL-Goitrin、(R, S)-Goitrin、R,S-goitrin）是板蓝根（Radix Isatidis）的主要成分之一，广泛用于传统中药中治疗发烧和清热。研究表明，去氧板蓝根苷具有抗病毒和抗内毒素活性。

体外研究

根据报告表格Spring的研究显示，去氧板蓝根苷不仅是抗流感病毒的有效成分，还显示出一定的毒性。

反应信息

• 作为反应物：
  描述：

  5-乙烯基-1,3-恶唑烷-2-硫酮 在 Chiralpak IC column 作用下， 以 乙腈 为溶剂， 生成 表告依春 、 DL-甲状腺肿素
  参考文献：
  名称：

  Antiviral activity of Isatidis Radix derived glucosinolate isomers and their breakdown products against influenza A in vitro/ovo and mechanism of action

  摘要：

  Ethnopharmacological relevance: Isatidis Radix, the sun-dried roots of Isatis indigotica Fortune ex Lindl., is one of the most usually used traditional Chinese medicines. For centuries, the herb has been employed in clinical practice for treatment of virus infection and inflammation. However, its active ingredients remain unclear.Aim of the study: In the present study, the anti-influenza virus activity of epiprogoitrin, progoitrin, epigoitrin and goitrin, the Isatidis Radix derived glucosinolate isomers and their breakdown products, was firstly evaluated in vitro and in ovo and their mechanism of action was investigated.Materials and methods: Epiprogoitrin, progoitrin, epigoitrin and goitrin were isolated from Isatidis Radix by chiral separation. In vitro and in ovo evaluations were performed on Madin-Darby canine kidney (MDCK) cells and embryonated eggs respectively, both using protocols including prevention, treatment and virus neutralization. Hemagglutination (HA) and neuraminidase (NA) inhibition assays were performed for further understanding of the antiviral mechanism.Results: Isatidis Radix derived glucosinolate isomers and their breakdown products all exhibited dose-dependent inhibition effect against influenza A virus (H1N1) without toxicity. The antiviral potency of the components was in the order of progoitrin > goitrin > epigoitrin > epiprogoitrin. The attachment of the constituents to the viral envelope conduced to the mechanism of their antiviral action without disturbing viral adsorption or budding.Conclusion: Taken together, these results are promising for further development of Isatidis Radix and may contribute an adjunct to pharmacotherapy for influenza virus infection.

  DOI：

  10.1016/j.jep.2020.112550
• 作为产物：
  描述：

  1-氨基-3-丁烯-2-醇 以70%的产率得到
  参考文献：
  名称：

  GARDRAT, C.;LATXAGUE, L.;PICARD, J. P., J. HETEROCYCL. CHEM., 27,(1990) N, C. 811-812

  摘要：

  DOI：

文献信息

• A new synthesis of dl-5-vinyloxazolidine-2-thione, a natural antithyroid factor
  作者：C. Gardrat、L. Latxague、J. P. Picard

  DOI：10.1002/jhet.5570270361

  日期：1990.3

  A new procedure for the preparation of DL-5-vinyloxazolidine-2-thione (goitrin) 3 via a facile and practical synthesis of the key intermediate DL-1-amino-3-buten-2-ol 2 is described.

  描述了通过关键中间体DL-1-氨基-3-丁烯-2-醇2的简便，实用合成来制备DL-5-乙烯基恶唑烷-2-硫酮（goitrin）3 的新方法。
• 一种5-乙烯基-2-硫代恶唑烷的制备方法
  申请人：天津大学

  公开号：CN109678812B

  公开（公告）日：2022-09-02

  本发明公开了一种5‑乙烯基‑2‑硫代恶唑烷的制备方法，步骤如下：(1)以丙烯醛和三甲基氰硅烷为原料，在碘化锌催化下反应得到2‑[(三甲基甲硅烷基)氧基]‑3‑丁烯腈；(2)在甲苯溶液中，以红铝溶液为还原剂，以碳酸钾、甲醇作为脱硅剂，使2‑[(三甲基甲硅烷基)氧基]‑3‑丁烯腈进行还原反应和脱硅反应，得到1‑氨基‑3‑丁烯‑2‑醇；(3)将1‑氨基‑3‑丁烯‑2‑醇与二硫化碳进行反应，以双氧水为脱硫剂，得到5‑乙烯基‑2‑硫代恶唑烷。本发明使用的脂肪链氰基还原剂为红铝溶液，相较于传统的氢化铝锂来说，操作条件简单，价格低廉。在还原反应中以甲苯为溶剂，而非传统的乙醚等易燃液体，反应条件更安全。而在步骤(3)成环反应中，以双氧水代替原有的硝酸铅做脱硫剂，可降低对环境的污染，安全环保。
• 一种抗病毒药物（R ,S）-告依春的合成方法
  申请人：天津大学

  公开号：CN109553587A

  公开（公告）日：2019-04-02

  本发明公开了一种抗病毒药物(R，S)‑告依春的合成方法，将硝基甲烷溶于合适的溶剂中，加入丙烯醛，在设定的温度下搅拌一段时间，将三乙胺溶于剩余的硝基甲烷中进行滴加，反应完成后，旋蒸除去溶剂和未反应的硝基甲烷，所得混合物经柱色谱分离可得到1‑硝基‑3‑丁烯‑2‑醇。将得到的1‑硝基‑3‑丁烯‑2‑醇用铁粉还原法还原硝基得到1‑氨基‑3‑丁烯‑2‑醇，1‑氨基‑3‑丁烯‑2‑醇进一步与二硫化碳发生成环反应，生成(R，S)‑告依春。采用本发明合成方法具有成本低、操作简单、安全环保的优点。
• 一种高纯度5-乙烯基恶唑烷-2-硫酮的制备方 法
  申请人：上海应用技术学院

  公开号：CN104447602B

  公开（公告）日：2017-01-11

  本发明公开了一种高纯度5‑乙烯基恶唑烷‑2‑硫酮的制备方法，首先以1‑氨基‑3‑丁烯‑2‑醇为起始原料，经硝酸铅水溶液配位，在氢氧化钾溶液的碱性环境中与CS2发生成环反应，过滤反应液，用乙酸乙酯提取，经分液、干燥、旋蒸后即得粗产品，再将含有粗产品的水溶液，通过制备型液相色谱仪分离纯化，在目标产物的保留时间段内接取流动相，旋蒸干燥后即得产品。本发明的方法步骤简单、操作方便、成本低廉、产量较高，单次制备量可达0.2~0.3 g，纯度为99.0%~99.5%。
• Degradation of 2-hydroxybut-3-enylglucosinolate (progoitrin)
  作者：Alexander J. Macleod、John T. Rossiter

  DOI：10.1016/s0031-9422(00)84763-9

  日期：1987.1

  Abstract Using a model system consisting of synthesized 2-hydroxybut-3-enylglucosinolate and a purified thioglucoside glucohydrolase preparation from Brassica napus , the effects of ascorbate, of Fe 2+ and of Cu 2+ were examined on the extent and course of glucosinolate degradation. Ascorbate was found to promote thioglucosidase activity to a considerable extent over the whole of the wide range of

  摘要 使用由合成的 2-羟基丁-3-烯基芥子油苷和来自欧洲油菜的纯化硫代葡萄糖苷葡萄糖水解酶制剂组成的模型系统，研究了抗坏血酸、Fe 2+ 和 Cu 2+ 对芥子油苷降解程度和过程的影响。发现抗坏血酸在所研究的广泛浓度范围内（0.024-400 mM）在相当程度上促进硫葡萄糖苷酶活性，最大（活化因子约 100）为 1.57 mM 抗坏血酸。Fe 2+ 轻微抑制反应，但通过将降解引导至 1-cyano-2-hydroxybut-3-ene 而不是 5-vinyloxazolidine-2-thione 并在低催化浓度下产生显着影响。Cu 2+ 具有类似的作用，但是该反应的强抑制剂。

表征谱图