4-氯-2,5-二甲基噻酚 | 59962-29-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚类
• 中文名称: 4-氯-2,5-二甲基噻酚
• 中文别名: 4-氯-2,5-二甲基苯硫酚；4-氯-2,5-二甲基噻吩
• 英文名称: 4-Chloro-2,5-dimethylbenzenethiol
• 英文别名: 4-chloro-2,5-dimethyl-thiophenol；4-Chlor-2.5-dimethyl-phenylmercaptan；5-Chlor-2-mercapto-p-xylol；4-Chlor-2,5-dimethyl-thiophenol；4-Chlor-thio-p-xylenol
• CAS: 59962-29-7
• 化学式: C₈H₉ClS
• 分子量: 172.678
• InChiKey: OJYSHGUXHULIBN-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：
  避免直接接触氧化物和空气。

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R23/24/25,R34
• 海关编码：
  2930909090
• 储存条件：
  在干性气体保护下，应将样品存放在密封的贮藏器中，并置于阴凉、干燥处保存。

反应信息

• 作为反应物：
  描述：

  4-氯-2,5-二甲基噻酚 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 、 三乙胺 、 肼 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成 CMB-086482-1
  参考文献：
  名称：

  ADME-Guided Design and Synthesis of Aryloxanyl Pyrazolone Derivatives To Block Mutant Superoxide Dismutase 1 (SOD1) Cytotoxicity and Protein Aggregation: Potential Application for the Treatment of Amyotrophic Lateral Sclerosis

  摘要：

  Amyotrophic lateral sclerosis (ALS) is an orphan neurodegenerative disease currently without a cure: The arylsulfanyl pyrazolone (ASP) scaffold was one of the active scaffolds identified in a cell-based high throughput screening assay targeting mutant Cu/Zn superoxide dismutase 1 (SOD 1) induced toxicity and aggregation as a marker for ALS. The initial ASP hit compounds were potent and had favorable ADME properties but had poor microsomal and plasma stability. Here, we identify the microsomal metabolite and describe synthesized analogues of these ASP compounds to address the rapid metabolism. Both in vitro potency and pharmacological properties of the ASP scaffold have been dramatically improved via chemical modification to the corresponding sulfone and ether derivatives. One of the ether analogues (13), with superior potency and in vitro pharmacokinetic properties, was tested in vivo for its pharmacokinetic profile, brain penetration, and efficacy in an ALS mouse model. The analogue showed sustained blood and brain levels in vivo and significant activity in the mouse model of ALS, thus validating the new aryloxanyl pyrazolone scaffold as an important novel therapeutic lead for the treatment of this neurodegenerative disorder.

  DOI：

  10.1021/jm2014277
• 作为产物：
  描述：

  2-氯-1,4-二甲基苯 在 二硫化碳 、 三氯化铝 、 二氧化硫 作用下， 生成 4-氯-2,5-二甲基噻酚
  参考文献：
  名称：

  US1993663

  摘要：

  公开号：

文献信息

• Propenoic acid derivatives
  申请人：AgrEvo UK Limited

  公开号：EP0517301A1

  公开（公告）日：1992-12-09

  Compounds of formula I wherein X is CH or N; n is 0, 1, 2 or 3; R¹ and R³, which may be the same or different, are alkyl, alkoxy or alkylthio, each of which is optionally substituted, halogen, nitro, cyano, COOR⁴, -NR⁵R⁶, CONR⁵R⁶, COR⁷ or R⁸S(O)q; or R¹ and an adjacent R³ group, or two adjacent R³ groups, together with the carbon atoms to which they are attached can form a 5 to 8 membered ring which can include 1 to 3 heteroatoms and may be substituted; R² is an optionally substituted aliphatic hydrocarbon radical, which may be unsaturated, aryl or heterocyclyl; R⁴ is hydrogen or an ester forming group; R⁵ and R⁶ are the same or different and are hydrogen, optionally substituted alkyl, acyl or aryl, or together with the nitrogen to which they are attached, form a 5 to 7 membered ring which can contain other hetero atoms; R⁷ is hydrogen, optionally substituted alkyl or aryl; R⁸ is optionally substituted alkyl or aryl; and q is 1 or 2, have fungicidal activity as do the intermediates of formula II wherein R⁹ is hydrogen or methyl, and of formula III

  化合物的公式I，其中X是CH或N; n为0、1、2或3; R¹和R³可以相同也可以不同，是烷基、烷氧基或烷硫基，每个基团都可以选择性地被取代，取代基可以是卤素、硝基、氰基、COOR⁴、-NR⁵R⁶、CONR⁵R⁶、COR⁷或R⁸S（O）q; 或者R¹和相邻的R³基团，或者两个相邻的R³基团，与它们连接的碳原子一起可以形成一个5到8个成员环，其中可以包含1到3个杂原子，并且可以被取代; R²是一个可以选择性取代的脂肪族碳氢基团，可以是不饱和的、芳香的或杂环基团; R⁴是氢或酯基形成基团; R⁵和R⁶相同或不同，是氢、可以选择性取代的烷基、酰基或芳基，或者与它们连接的氮一起形成一个5到7个成员环，其中可以含有其他杂原子; R⁷是氢、可以选择性取代的烷基或芳基; R⁸是可以选择性取代的烷基或芳基; q为1或2，具有杀真菌活性，公式II中的中间体在R⁹为氢或甲基的情况下，公式III也具有杀真菌活性。
• Phenylsulfonyl nitromethanes as aldose reductase inhibitors
  申请人：Imperial Chemical Industries PLC

  公开号：US05153227A1

  公开（公告）日：1992-10-06

  The invention concerns novel pharmaceutical compositions for use in the treatment of certain complications of diabetes and galactosemia and which contain a nitromethane derivative (or its non-toxic salt) as active ingredient. The nitromethane derivatives are inhibitors of the enzyme aldose reductase. Many of the inhibitors are novel and are provided, together with processes for their manufacture and use, as further features of the invention.

  这项发明涉及一种新型药物组合物，用于治疗糖尿病和半乳糖血症的某些并发症，并含有硝基甲烷衍生物（或其非毒性盐）作为活性成分。硝基甲烷衍生物是醛糖还原酶酶的抑制剂。其中许多抑制剂是新颖的，并且作为该发明的进一步特征，提供了它们的制造和使用过程。
• Imidazole derivatives as therapeutic agents
  申请人：Knoll Aktiengesellschaft

  公开号：US06215001B1

  公开（公告）日：2001-04-10

  Compounds of the formula I and pharmaceutically acceptable salts thereof in which R1 represents hydrogen, halo, cyano, cyanoalkyl, alkyl, alkoxy, phenoxy, phenyl, alkoxycarbonyl, —NR13R14, —N(R15)SO2R16, halogenated alkoxy, halogenated alkyl, arylalkoxy, hydroxy, phenylalkyl, alkoxycarbonylvinyl, —S(O)nR7, alkoxycarbonylalkyl, carboxyalkyl, —CONR13R12 carbamoylvinyl, —OSO2R21, 4,5-dihydrothiazol-2-yl, 4,4-dimethyl-2-oxazolin-2-yl or —NR60R61; or R1 represents a group of formula —(O)z—L3G wherein z equals 0 or 1, L3 represents a C1-4 alkylene chain, G represents a group of formula a), b), c), or d): a) —NR22R23; b) —S(O)mR26; c) CONR27R28; d) —OR29; R2 and R3 independently represent hydrogen, halo, alkyl, alkoxy, —NR13R14, halogenated alkoxy, halogenated alkyl, hydroxy, —S(O)nR7 or —NR60R61; L1 represents e) a bond, or f) alkylene, cycloalkylene or cycloalkylidene; T represents a bond or O, S, SO, SO2, a carbonyl group, or 1,3-dioxolan-2-ylidene; L2 represents alkylene, cycloalkylene, or cycloalkylidene; R6 represents hydrogen or alkyl (optionally substituted by alkoxycarbonyl or hydroxy); Q represents a C1-9 alkylene chain (optionally substituted by alkyl or hydroxy); and Y represents an optionally substituted imidazole ring; which are antiinflammatory, antiallergic and immunodulant agents. Compositions containing these compounds and processes to make them are also disclosed.

  公式 I 及其药学上可接受的盐，其中 R1 代表氢、卤素、氰基、氰基烷基、烷基、烷氧基、苯氧基、苯基、烷氧羰基、-NR13R14、-N（R15）SO2R16、卤代烷氧基、卤代烷基、芳基烷氧基、羟基、苯基烷基、烷氧羰基乙烯基、-S（O）nR7、烷氧羰基烷基、羧基烷基、-CONR13R12氨基乙烯基、-OSO2R21、4,5-二氢噻唑-2-基、4,4-二甲基-2-噁唑烷-2-基或-NR60R61；或 R1 代表公式-(O)z-L3G 的基团，其中 z 等于 0 或 1，L3 代表 C1-4 烷基链，G 代表公式 a)、b)、c) 或 d) 的基团：a) -NR22R23；b) -S（O）mR26；c) -CONR27R28；d) -OR29；R2 和 R3 分别代表氢、卤素、烷基、烷氧基、-NR13R14、卤代烷氧基、卤代烷基、羟基、-S（O）nR7 或-NR60R61；L1 代表 e) 键或 f) 烷基、环烷基或环烷基亚甲基；T 代表键或 O、S、SO、SO2、羰基团或 1,3-二氧杂环戊二烯基；L2 代表烷基、环烷基或环烷基亚甲基；R6 代表氢或烷基（可选地被烷氧羰基或羟基取代）；Q 代表 C1-9 烷基链（可选地被烷基或羟基取代）；Y 代表可选地取代的咪唑环；这些化合物是抗炎、抗过敏和免疫增强剂。还公开了含有这些化合物的组合物和制备它们的过程。
• Phenoxy-, phenylthio-, benzoyl-alkyleneaminoalkylene-imidazole
  申请人：Knoll Aktiengesellschaft

  公开号：US06031109A1

  公开（公告）日：2000-02-29

  Compounds of formula I ##STR1## where R.sub.1 -R.sub.3, L.sub.1, T, L.sub.2 --N--Q--Y and R.sub.6 are as defined in the specification, and pharmaceutically acceptable salts thereof which are antiinflammatory, antiallergic and immunomodulant agents, compositions containing these compounds and processes to make them.

  式子I的化合物，其中R.sub.1-R.sub.3，L.sub.1，T，L.sub.2--N--Q--Y和R.sub.6的定义如说明书中所述，并且其药学上可接受的盐是抗炎，抗过敏和免疫调节剂，包含这些化合物的组合物以及制造它们的过程。
• Imidazole derivatives for blocking the release of arachidonic acid from phospholipids
  申请人：Abbott Laboratories

  公开号：US06326500B1

  公开（公告）日：2001-12-04

  Compounds of formula (I) and salts thereof, wherein R1 is hydrogen, halo, cyano, cyanoalkyl, alkyl, alkoxy, phenoxy, phenyl, alkoxycarbonyl, —NR13R14, —N(R15)SO2R16, haloalkoxy, haloalkyl, arylalkoxy, hydroxy, phenylalkyl, alkoxycarbonylvinyl, —SOnR7, alkoxycarbonylalkyl, carboxylalkyl, —CONR11R12, carbamoylvinyl, —O—SO2R21, 4,5-dihydrothiazol-2-yl, 4,4-dimethyl-2-oxazolin-2-yl, —NR60R61 or —(O)z—L3—G (G=−NR22R23, —SOmR26, CONR27R28 or —OR29); R2 and R3 are independently hydrogen halo, alkyl, alkoxy, —NR13R14, haloalkoxy, haloalkyl, hydroxy, —SOnR7 or —NR60R61; L1 is a bond, alkylene, cycloalkylene or cycloalkylidene; T is a bond, O, S, SO, SO2, CO or 1,3-dioxolan-2-ylidene; L2 is alkylene, cycloalkylene or cycloalkylidene; R6 is hydrogen or alkyl; Q is alkylene; and Y is imidazolyl, which are antiinflammatory, antiallergic and immunodulant agents. Compositions containing these compounds and processes to make them are also disclosed.

  化合物式（I）及其盐，其中R1为氢，卤，氰，氰基烷基，烷基，烷氧基，苯氧基，苯基，烷氧羰基，-NR13R14，-N（R15）SO2R16，卤代烷氧基，卤代烷基，芳基烷氧基，羟基，苯基烷基，烷氧羰基乙烯基，-SOnR7，烷氧羰基烷基，羧基烷基，-CONR11R12，氨基乙烯基，-O-SO2R21，4,5-二氢噻唑-2-基，4,4-二甲基-2-噁唑烷-2-基，-NR60R61或-(O)z-L3-G（G= -NR22R23，-SOmR26，CONR27R28或-OR29）;R2和R3独立地为氢，卤，烷基，烷氧基，-NR13R14，卤代烷氧基，卤代烷基，羟基，-SOnR7或-NR60R61;L1为键，烷基，环烷基或环烷基亚甲基;T为键，O，S，SO，SO2，CO或1,3-二氧杂环戊烷-2-基亚甲基;L2为烷基，环烷基或环烷基亚甲基;R6为氢或烷基;Q为烷基;Y为咪唑基，具有抗炎，抗过敏和免疫调节作用。还公开了含有这些化合物的组合物和制备它们的过程。

表征谱图