增效砜 | 120-62-7

• 物质功能分类: 化学试剂 - 有机试剂 - 砜、亚砜类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 中文名称: 增效砜
• 中文别名: 5-[2-(辛基亚磺酰)丙基]-1，3-苯并二氧杂环戊烷；亚砜；1-甲基-2-(3，4-亚甲二氧基苯基)-乙基辛基亚砜(简称异黄樟素正辛基亚砜)；亚砜
• 英文名称: Piperonyl sulfoxide
• 英文别名: 5-(2-octylsulfinylpropyl)-1,3-benzodioxole
• CAS: 120-62-7
• 化学式: C₁₈H₂₈O₃S
• 分子量: 324.5
• InChiKey: ATTZFSUZZUNHBP-UHFFFAOYSA-N

物化性质

• 沸点：
  432.8°C (rough estimate)
• 密度：
  1.1040 (rough estimate)
• 物理描述：
  Piperonyl sulfoxide is a clear pale yellow to amber viscous liquid with a sweetish smell. (NTP, 1992)
• 颜色/状态：
  PALE YELLOW, VISCOUS OIL
• 气味：
  SWEET-SMELLING
• 闪点：
  greater than 200 °F (NTP, 1992)
• 溶解度：
  less than 0.1 mg/mL at 72° F (NTP, 1992)
• 稳定性/保质期：
  STABLE UNDER NORMAL CONDITIONS
• 分解：
  WHEN HEATED TO DECOMPOSITION, IT EMITS HIGHLY TOXIC FUMES OF /SULFUR OXIDES/.

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  4

ADMET

代谢

A和B磺酰亚砜对映体1,2-亚甲二氧基-4-(2-辛基亚磺酰丙基)苯在小鼠口服给药后的主要代谢途径涉及甲二氧基苯基团(MDP)的裂解和甲基碳作为二氧化碳的呼出。肝脏微粒体的混合功能氧化酶对含有MDP部分的几种化合物进行了去甲基化。

MAJOR METABOLIC PATHWAY FOR A & B SULFOXIDE DIASTEREOMERS OF 1,2-METHYLENEDIOXY-4-(2-OCTYLSULFINYL PROPYL)BENZENE AFTER ORAL ADMINISTRATION TO MICE INVOLVED THE CLEAVAGE OF THE METHYLENEDIOXYPHENYL (MDP) MOIETY & EXPIRATION OF THE METHYLENE CARBON AS CARBON DIOXIDE. MIXED-FUNCTION OXIDASES OF LIVER MICROSOMES DEMETHYLATED SEVERAL COMPOUNDS CONTAINING THE MDP MOIETY.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

神经毒素 - 其他中枢神经系统神经毒素

Neurotoxin - Other CNS neurotoxin

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 相互作用

增效剂，增强除虫菊酯的杀虫效力。

...SYNERGIST TO INCR INSECTICIDAL POTENCY OF PYRETHRINS.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

在甲氧基二氧基苯基增效剂中，至少已显示以下物质在服用某些巴比妥类药物后可增加睡眠时间，以及/或抑制哺乳动物微粒体酶：胡椒基丁氧化物；胡椒基环己烯；磺酰氧化物...

OF THE METHYLENEDIOXYPHENYL SYNERGISTS, AT LEAST THE FOLLOWING HAVE BEEN SHOWN TO INCR SLEEPING TIME FOLLOWING ADMIN OF CERTAIN BARBITURATES &/OR TO INHIBIT MAMMALIAN MICROSOMAL ENZYMES: PIPERONYL BUTOXIDE; PIPERONYL CYCLONENE; SULFOXIDE...

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

可能是由于抑制了肝脏酶的作用，胡椒基丁醚和亚砜都降低了以7,10-(14)C-苯并芘形式引入的放射性物质从血液中清除并在胆汁中排泄的速度。

PRESUMABLY AS A RESULT OF INHIBITING LIVER ENZYMES, BOTH PIPERONYL BUTOXIDE & SULFOXIDE REDUCED THE RATE AT WHICH RADIOACTIVITY INTRODUCED IN THE FORM OF 7,10-(14)C-BENZPYRENE WAS CLEARED FROM THE BLOOD & EXCRETED IN THE BILE.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

当通过口服、腹膜内或静脉内给药时，胡椒基砜干扰了大鼠静脉注射的3,4-苯并芘的快速消除。

WHEN ADMINISTERED ORALLY, INTRAPERITONEALLY OR INTRAVENOUSLY PIPERONYL SULFOXIDE INTERFERRED WITH RAPID ELIMINATION OF INTRAVENOUSLY INJECTED 3,4-BENZPYRENE IN RATS.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 海关编码：
  2932999014
• 安全说明：
  S24/25

制备方法与用途

理化性质

亚砜是一种含有两个碳原子的亚磺酰基（SO）官能团的化合物，属于极性官能团。它是硫化物的氧化衍生物。

亚砜是指由亚硫酰基与烃基R结合而成的一类化合物，如二甲基亚砜、二乙基亚砜和苄苯亚砜等。在亚砜中，氧原子呈负离子状态，并具有很强的极性和强氧化性。亚砜类化合物可能具有光学活性，在低温下为固体，一般可溶于水、乙醇、乙醚。它们能被还原剂还原成硫醚，被氧化剂氧化成砜，还能与硝酸形成盐。这类化合物可以通过硫醚氧化或通过芳烃与氯化亚砜进行傅特尔-克拉符兹反应制备。

亚砜具有多种重要的化学反应性：

1. 亚硫酰基的α位阴碳离子反应性强，容易与卤代烷基化合物、羰基化合物以及烯烃等发生反应；
2. 能够与酸酐引起Pummerer转位反应；
3. 具有β位氢的亚砜通过加热分解可以生成烯烃和亚磺酸。

类别 农药 毒性分级

• 中毒

急性毒性

• 口服 - 大鼠 LD50: 2000 毫克/公斤

可燃性危险特性

• 燃烧时产生有毒硫氧化物气体

储运特性

• 库房通风、低温干燥保存与运输；与食品原料分开存放

灭火剂

• 干粉、泡沫、砂土

文献信息

• BENZOTHIOPHENE INHIBITORS OF RHO KINASE
  申请人：Kahraman Mehmet

  公开号：US20080021026A1

  公开（公告）日：2008-01-24

  The present invention relates to compounds and methods which may be useful as inhibitors of Rho kinase for the treatment or prevention of disease.

  本发明涉及化合物和方法，这些化合物和方法可能作为Rho激酶的抑制剂在治疗或预防疾病方面有用。
• N-type calcium channel blockers
  申请人：Pajouhesh Hassan

  公开号：US20050165065A1

  公开（公告）日：2005-07-28

  The invention relates to novel 3-amino pyrrolidine derivatives, as well as methods for modulating calcium channel activity and for treating conditions associated with calcium channel function. In particular, the compounds generally contain at least one benzhydril moiety, and are useful in treating conditions which benefit from blocking calcium ion channels.

  这项发明涉及新型3-氨基吡咯烷衍生物，以及调节钙通道活性和治疗与钙通道功能相关疾病的方法。具体来说，这些化合物通常至少含有一个苯基甲酰基团，可用于治疗受益于阻断钙离子通道的疾病。
• [EN] AZA PYRIDONE ANALOGS USEFUL AS MELANIN CONCENTRATING HORMONE RECEPTOR-1 ANTAGONISTS<br/>[FR] ANALOGUES D'AZAPYRIDONE UTILES COMME ANTAGONISTES DU RÉCEPTEUR 1 DE L'HORMONE CONCENTRANT LA MÉLANINE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2010104818A1

  公开（公告）日：2010-09-16

  MCHR1 antagonists are provided having the following Formula (I): A1 and A2 are independently C or N; E is C or N; Q1, Q2, and Q3 are independently C or N provided that at least one of Q1, Q2, and Q3 is N but not more than one of Q1, Q2, and Q3 is N; D1 is a bond, -CR8R9 X-, -XCR8R9-, -CHR8CHR9-, -CR10=CR10'-, -C≡C-, or 1,2-cyclopropyl; X is O, S or NR11; R1, R2, and R3 are independently selected from the group consisting of hydrogen, halogen, lower alkyl, lower cycloalkyl, -CF3, -OCF3, -OR12 and -SR12; G is O, S or -NR15; D2 is lower alkyl, lower cycloalkyl, lower alkylcycloalkyl, lower cycloalkylalkyl, lower cycloalkoxyalkyl or lower alkylcycloalkoxy or when G is NR15, G and D2 together may optionally form an azetidine, pyrrolidine or piperidine ring; Z1 and Z2 are independently hydrogen, lower alkyl, lower cycloalkyl, lower alkoxy, lower cycloalkoxy, halo, -CF3, -OCONR14R14', -CN, -CONR14R14', -SOR12, -SO2R12, -NR14COR14', -NR14CO2R14', -CO2R12, NR14SO2R12 or COR12; R5, R6, and R7 are independently selected from the group consisting of hydrogen lower alkyl, lower cycloalkyl, -CF3, -SR12, lower alkoxy, lower cycloalkoxy, -CN, -CONR14R14', SOR12, SO2R12, NR14COR14', NR14CO2R12, CO2R12, NR14SO2R12 and -COR12; R8, R9, R10, R10', R11 are independently hydrogen or lower alkyl; R12 is lower alkyl or lower cycloalkyl; R14 and R14' are independently H, lower alkyl, lower cycloalkyl or R14 and R14' together with the N to which they are attached form a ring having 4 to 7 atoms; and R15 is independently selected from the group consisting of hydrogen and lower alkyl. Such compounds are useful for the treatment of MCHR1 mediated diseases, such as obesity, diabetes, IBD, depression, and anxiety.

  MCHR1拮抗剂具有以下化学式（I）：A1和A2独立地为C或N；E为C或N；Q1、Q2和Q3独立地为C或N，但至少其中一个为N，但不超过一个为N；D1为键，-CR8R9 X-，-XCR8R9-，-CHR8CHR9-，-CR10=CR10'-，-C≡C-，或1,2-环丙基；X为O、S或NR11；R1、R2和R3独立地从氢、卤素、低烷基、低环烷基、-CF3、-OCF3、-OR12和-SR12组成的群体中选择；G为O、S或-NR15；D2为低烷基、低环烷基、低烷基环烷基、低环烷基烷基、低环烷氧基烷基或低烷基环烷氧基，或当G为NR15时，G和D2一起可以选择形成氮杂环丙烷、吡咯烷或哌啶环；Z1和Z2独立地为氢、低烷基、低环烷基、低烷氧基、低环烷氧基、卤素、-CF3、-OCONR14R14'、-CN、-CONR14R14'、-SOR12、-SO2R12、-NR14COR14'、-NR14CO2R14'、-CO2R12、NR14SO2R12或COR12；R5、R6和R7独立地从氢、低烷基、低环烷基、-CF3、-SR12、低烷氧基、低环烷氧基、-CN、-CONR14R14'、SOR12、SO2R12、NR14COR14'、NR14CO2R12、CO2R12、NR14SO2R12和-COR12组成的群体中选择；R8、R9、R10、R10'、R11独立地为氢或低烷基；R12为低烷基或低环烷基；R14和R14'独立地为H、低烷基、低环烷基或R14和R14'与其连接的N一起形成具有4至7个原子的环；R15独立地从氢和低烷基组成的群体中选择。这些化合物对于治疗MCHR1介导的疾病，如肥胖症、糖尿病、炎症性肠病、抑郁症和焦虑症非常有用。
• NEW STRIGOLACTONE ANALOGUES AND THE USE THEREOF FOR THE TREATMENT OF PLANTS
  申请人：INSTITUT NATIONAL DE LA RECHERCHE AGRONOMIQUE

  公开号：US20150141255A1

  公开（公告）日：2015-05-21

  A compound of general formula (I): in which X represents O, S, NH or an N-alkyl radical, R 1 and R 2 , identical or different, each represent H or a C 1 -C 10 hydrocarbon radical, R 1 and R 2 not both representing H, R 3 represents a C 1 -C 10 hydrocarbon radical, and R represents a phenyl radical monosubstituted or disubstituted by a substituent Y and, if applicable, a substituent Z, chosen from Cl, Br, I and CF 3 , or R represents a C═R 4 (R 5 ) radical in which R 4 represents an hydrocarbon radical and R 5 represents a linear or branched, saturated or unsaturated, hydrocarbon radical, optionally substituted, a COR 6 group or a CO 2 R 6 group, where R 6 represents a hydrogen atom or a linear or branched, saturated or unsaturated, hydrocarbon radical. This compound can be used for the treatment of higher plants for controlling their growth and architecture.

  通式（I）的化合物： 其中X代表O、S、NH或N-烷基基团，R1和R2，相同或不同，各自代表H或C1-C10烃基，R1和R2不同时代表H，R3代表C1-C10烃基，R代表被取代基团Y和如适用的取代基团Z选择自Cl、Br、I和CF3的苯基单取代或双取代基团，或R代表C═R4（R5）基团，其中R4代表烃基团，R5代表线性或支链、饱和或不饱和、可选择取代的烃基团、COR6基团或CO2R6基团，其中R6代表氢原子或线性或支链、饱和或不饱和的烃基团。该化合物可用于治疗高等植物，控制其生长和结构。
• [EN] PYRAZOLE DERIVATIVES USEFUL AS INHIBITORS OF FAAH<br/>[FR] DÉRIVÉS DE PYRAZOLE UTILES COMME INHIBITEURS DE FAAH
  申请人：MERCK & CO INC

  公开号：WO2009151991A1

  公开（公告）日：2009-12-17

  The present invention is directed to certain imidazole derivatives which are useful as inhibitors of Fatty Acid Amide Hydrolase (FAAH). The invention is also concerned with pharmaceutical formulations comprising these compounds as active ingredients and the use of the compounds and their formulations in the treatment of certain disorders, including osteoarthritis, rheumatoid arthritis, diabetic neuropathy, postherpetic neuralgia, skeletomuscular pain, and fibromyalgia, as well as acute pain, migraine, sleep disorder, Alzheimer disease, and Parkinson's disease

  本发明涉及某些咪唑衍生物，其可用作脂肪酰胺水解酶（FAAH）的抑制剂。该发明还涉及包含这些化合物作为活性成分的药物配方，以及这些化合物及其配方在治疗某些疾病中的使用，包括骨关节炎、类风湿性关节炎、糖尿病神经病变、带状疱疹后神经痛、骨骼肌肉疼痛和纤维肌痛，以及急性疼痛、偏头痛、睡眠障碍、阿尔茨海默病和帕金森病。

表征谱图