6-异硫氰基己烷-2-酮 | 153495-59-1

• 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: 6-异硫氰基己烷-2-酮
• 英文名称: 6-isothiocyanatohexan-2-one
• 英文别名: 2-oxohexyl isothiocyanate；sulphoraphane；2-oxohexyl ITC；6-isothiocyanato-2-hexanone；2-Hexanone, 6-isothiocyanato-
• CAS: 153495-59-1
• 化学式: C₇H₁₁NOS
• 分子量: 157.236
• InChiKey: KXJVOLXLYNDZME-UHFFFAOYSA-N

物化性质

• 沸点：
  280.6±23.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  61.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-异硫氰基己烷-2-酮 在 盐酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 methyl-N-(5-oxohexyl)-carbamodithioate
  参考文献：
  名称：

  PROCESS FOR THE SYNTHESIS OF ISOTHIOCYANATES AND DERIVATIVES THEREOF AND USES OF SAME

  摘要：

  一种合成一般式为（I）SCN-R1-R4-R2（I）的异硫氰酸酯的方法，其中R1和R2分别独立地表示烷基-芳基或芳基基团，R4表示羰基、亚磺酰基、磺酰基或硫醚基及其衍生物，包括通过在碳硫化物和双叔丁基二碳酸酯的存在下反应具有通式（II）NH2-R1-R4-R2（II）的烷基烷基胺，形成相应的上述异硫氰酸酯的步骤，以及通过该方法获得的化合物及其用途。

  公开号：

  US20130142739A1
• 作为产物：
  描述：

  1-Boc-2-哌啶酮 在 盐酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 氯仿 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 6-异硫氰基己烷-2-酮
  参考文献：
  名称：

  Design and synthesis of bifunctional isothiocyanate analogs of sulforaphane: correlation between structure and potency as inducers of anticarcinogenic detoxication enzymes

  摘要：

  Thirty-five bifunctional isothiocyanates were synthesized as structural analogs of sulforaphane [(-)-l-isothiocyanato-4(R)-(methylsulfinyl)butane] that was recently isolated from broccoli as the principal and very potent inducer of detoxication (phase 2) enzymes in mouse tissues and murine hepatoma cells (Hepa 1c1c7) in culture (Zhang, Y.; Talalay, P.; Cho, C.-G.; Posner, G. Il. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 2399-2403). Determination of the potency of each analog in inducing NAD(P)H:quinone reductase, a phase 2 detoxication enzyme, has allowed generalizations concerning the relation of structure and activity. The most potent analogs were bifunctional derivatives in which the isothiocyanate group was separated from a methylsulfonyl or an acetyl group by three or four carbon atoms, and in some of which these groups were conformationally restricted. Among these analogs, the bicyclic ketoisothiocyanate (+/-)-exo-2-acetyl-6-isothiocyanatonorbornane (30) was a very potent inducer (comparable to sulforaphane) of quinone reductase in hepatoma cells, and it also induced both quinone reductase and glutathione transferases in several mouse organs in vivo. This and related bicyclic ketoisothiocyanates represent potent phase 2 enzyme inducers that are relatively easily synthesized and that may be more stable metabolically than the natural sulfoxide sulforaphane.

  DOI：

  10.1021/jm00027a021

文献信息

• Stabilized sulforaphane
  申请人：Dagan Ido Dov

  公开号：US20080176942A1

  公开（公告）日：2008-07-24

  A method of stabilizing sulforaphane is provided. The method includes contacting sulforaphane, or an analog thereof, and a cyclodextrin to form a complex between the sulforaphane, or analog thereof, and the cyclodextrin.

  提供了一种稳定硫代异硫氰酸酯的方法。该方法包括将硫代异硫氰酸酯或其类似物与环糊精接触，以形成硫代异硫氰酸酯或其类似物与环糊精之间的复合物。
• Prevention and Treatment of Oxidative Stress Disorders by compounds which elevate intracellular levels of glutathione or Phase II Detoxification Enzymes
  申请人：Brassica Foundation for Chemoprotection Research, Inc.

  公开号：EP2138170A2

  公开（公告）日：2009-12-30

  The present invention generally relates to the field of treating oxidative stress disorders by administering a pharmaceutically effective amount of a compound that elevates the intracellular levels of glutathione or intracelluar levels of at least one Phase II detoxification enzyme in animal tissue. The present invention also relates to the field of protecting a subject from photooxidation or oxidative stress disorders by administering a pharmaceutically effective amount of a compound that elevates the intracellular levels of glutathione or intracellular levels of at least one Phase II detoxification enzyme in the subject. The present invention also relates to a pharmaceutical composition useful for the treatment of oxidative stress disorders.

  本发明一般涉及治疗氧化应激紊乱的领域，其方法是施用一种药学有效量的化合物，该化合物能提高动物组织中谷胱甘肽的细胞内水平或至少一种II期解毒酶的细胞内水平。本发明还涉及通过给药有效量的化合物来保护受试者免受光氧化或氧化应激紊乱的领域，该化合物能提高受试者体内谷胱甘肽的细胞内水平或至少一种II期解毒酶的细胞内水平。本发明还涉及一种用于治疗氧化应激紊乱的药物组合物。
• Zusammensetzung zur Hautaufhellung enthaltend Sulforaphan oder Sulforaphen oder deren Derivate
  申请人：Henkel AG & Co. KGaA

  公开号：EP2163238A2

  公开（公告）日：2010-03-17

  Gegenstand der vorliegenden Anmeldung sind kosmetische oder dermatologische Zusammensetzungen zur Aufhellung der Haut, die 8-Hexadecen-1,16-dicarbonsäure und mindestens eine Substanz, ausgewählt aus der Gruppe, bestehend aus Sulforaphan, Sulforaphen, Sulforaphan-Analoga und Sulforaphen-Analoga, enthalten.

  本申请涉及用于美白皮肤的化妆品或皮肤科组合物，该组合物包含 8-十六烯-1,16-二羧酸和至少一种选自由莱菔硫烷、莱菔硫烷、莱菔硫烷类似物和莱菔硫烷类似物组成的组的物质。
• Stabilized Sulforaphane
  申请人：Pharmagra Labs, Inc.

  公开号：EP2532352A1

  公开（公告）日：2012-12-12

  A method of stabilizing sulforaphane is provided. The method includes contacting sulforaphane, or an analog thereof, and a cyclodextrin to form a complex between the sulforaphane, or analog thereof, and the cyclodextrin.

  提供了一种稳定莱菔硫烷的方法。该方法包括将莱菔硫烷或其类似物与环糊精接触，以在莱菔硫烷或其类似物与环糊精之间形成复合物。
• Prevention and treatment of oxidative stress disorders by compounds which elevate intracellular levels of glutathione or phase II detoxification enzymes
  申请人：Brassica Foundation for Chemoprotection Research, Inc.

  公开号：EP2698153A1

  公开（公告）日：2014-02-19

  The present invention generally relates to the field of treating oxidative stress disorders, by administering a pharmaceutically effective amount of a compound that elevates the intracellular levels of glutathione or intracellular levels of at least one Phase II detoxification enzyme in animal tissue. The present invention also relates to the field of protecting a subject from oxidative stress disorders by administering a pharmaceutically effective amount of a compound that elevates the intracellular levels of glutathione or intracellular levels of at least one Phase II detoxification enzyme in the subject. The present invention also relates to a pharmaceutical composition useful for the treatment of oxidative stress disorders. The oxidative stress disorders that are treated or prevented are Alzheimer's disase and aging.

  本发明一般涉及治疗氧化应激紊乱的领域，方法是施用一种药学有效量的化合物，该化合物能提高动物组织中谷胱甘肽的细胞内水平或至少一种II期解毒酶的细胞内水平。本发明还涉及通过给药有效量的化合物来保护受试者免受氧化应激紊乱的领域，该化合物能提高受试者体内谷胱甘肽的细胞内水平或至少一种II期解毒酶的细胞内水平。本发明还涉及一种用于治疗氧化应激紊乱的药物组合物。可治疗或预防的氧化应激紊乱包括阿尔茨海默氏症和衰老。