N-methyl-6-cyano-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide | 134122-03-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N-methyl-6-cyano-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide
• 英文别名: 6-cyano-3-hydroxy-N,2,2-trimethylchromene-4-carbothioamide
• CAS: 134122-03-5
• 化学式: C₁₄H₁₄N₂O₂S
• 分子量: 274.343
• InChiKey: XDVJQPZAQULSNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  97.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methyl-6-cyano-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide 在 钾硼氢 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 trans-6-cyano-3,4-dihydro-2,2-dimethyl-3-<(methylsulfonyl)oxy>-N-methyl-2H-1-benzopyran-4-thiocarboxamide
  参考文献：
  名称：

  Relaxant activity of 6-cyano-2,2-dimethyl-2H-1-benzopyran-4-carboxamides and -thiocarboxamides and their analogs in guinea pig trachealis

  摘要：

  Structural modifications of the potassium channel activator cromakalim (1) are described in which the amide moiety at C-4 has been replaced by carboxamide and thiocarboxamide functions. Analogues in which the hydroxyl group at C-3 has been oxidized or removed are also disclosed. Such analogues display an interesting profile of smooth muscle relaxant activity in the guinea pig isolated trachea, not all of which appears to result from the opening of potassium channels, but few compounds retain useful in vivo activity. However, one compound in particular, 6-cyano-2,2-dimethyl-N-methyl-2H-1-benzopyran-4-thiocarboxamide (13) was shown to be a potent potassium channel activator in vitro and to provide prolonged protection to guinea pigs from the respiratory effects of inhaled histamine.

  DOI：

  10.1021/jm00112a037
• 作为产物：
  描述：

  6-cyano-2,2-dimethyl-2H-1-benzopyran-3-one 、 异硫氰酸甲酯 以 ice-water 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-methyl-6-cyano-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide
  参考文献：
  名称：

  Benzopyran derivatives

  摘要：

  以公式（I）表示的苯并吡喃衍生物：其中X表示=O，=S，=N-Z（Z表示低碳基团等），或=CHNO.sub.2；Y表示取代氨基团，烷氧基团，烷硫基团等，而R.sub.1，R.sub.2，R.sub.3，R.sub.4，R.sub.5，R.sub.6和R.sub.7分别表示氢原子，低碳基团等。这些苯并吡喃衍生物表现出K.sup.+通道激活活性，并广泛应用于抗哮喘药、抗癫痫药等。

  公开号：

  US05412117A1

文献信息

• Soil release agents having allylderived sulfonated end caps
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0357280A2

  公开（公告）日：1990-03-07

  The present invention relates to novel soil release agents, which are particular sulfonated linear terephthalate ester oligomers (S.T.E. oligomers). The S.T.E. oligomers are especially suitable for formulation into laundry products such as laundry detergents or fabric conditioners. Thus formulated, they provide effective soil release treatments for fabrics laundered in the home. The S.T.E. oligomers can be made by radical-initiated sul­fonation of an allyl end-capped oligomeric ester precursor, and in the preferred embodiments, comprise a high proportion of disulfon­ate or sulfinate-sulfonate end-capping groups.

  本发明涉及新型脱土剂，特别是磺化线性对苯二甲酸酯低聚物（S.T.E.低聚物）。S.T.E. 低聚物特别适合配制成洗衣产品，如洗衣粉或织物护理剂。这样配制出来的产品可对家庭洗涤的织物进行有效的土壤释放处理。S.T.E. 低聚物可通过烯丙基末端封端的低聚物酯前体的自由基引发磺化反应制成，在优选的实施方案中，S.T.E. 低聚物包含高比例的二磺酸盐或亚硫酸盐-磺酸盐末端封端基团。
• Ether carboxylate detergent builders
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0367296A2

  公开（公告）日：1990-05-09

  Provided herein are ether carboxylate builder compositions comprising a combination of tartrate monosuccinic acid (or salts thereof) and tartrate disuccinic acid (or salts thereof). Such mixtures can be prepared by reacting water-soluble, mixed maleic acid salts with mixed tartaric acid salts. Both components of the resulting ether carboxylate mixture act as sequestering agents and are useful as detergency builders. Detergent and laundry additive compositions incorporating these ether carboxylates can be pre­pared without use of detergent builder components containing phosphorus or nitrogen.

  本文提供的醚羧酸盐促进剂组合物包含酒石酸单琥珀酸盐（或其盐类）和酒石酸二琥珀酸盐（或其盐类）的组合。这种混合物可通过水溶性混合马来酸盐与混合酒石酸盐反应制备。由此产生的醚羧酸盐混合物中的两种成分都可用作螯合剂和去污剂。制备含有这些醚羧酸盐的洗涤剂和洗衣添加剂组合物时，无需使用含磷或氮的洗涤剂增效剂成分。
• NOVEL BENZOPYRAN DERIVATIVE
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：EP0541807A1

  公开（公告）日：1993-05-19

  A benzopyran derivative represented by general formula (I), which has a K⁺ channel activating effect and so is widely applicable for treating, for example, asthma and epilepsy, wherein X represents =O, =S, =N-Z (wherein Z represents lower alkyl, etc.), or = CHNO₂; Y represents substituted amino, alkoxy, alkylthio, etc.; and R₁ to R₇ represent each hydrogen, lower alkyl, etc.

  通式(I)代表的苯并吡喃衍生物，具有激活K⁺通道的作用，因此广泛用于治疗哮喘和癫痫等，其中X代表＝O、＝S、＝N-Z（其中Z代表低级烷基等）或＝CHNO₂；Y代表取代的氨基、烷氧基、烷硫基等；R₁至R₇各自代表氢、低级烷基等。
• US5412117A
  申请人：——

  公开号：US5412117A

  公开（公告）日：1995-05-02
• [EN] BENZOPYRAN DERIVATIVES
  申请人：BEECHAM GROUP PLC

  公开号：WO1990014346A1

  公开（公告）日：1990-11-29

  (EN) A compound of formula (I) or, where appropriate, a pharmaceutically acceptable salt, ester or amide thereof, or a pharmaceutically acceptable solvate thereof, wherein: X represents O or S; Y represents N or N+-O- or a moiety CR7 wherein R7 is as defined below; Z represents O, CH2, NR, S(O)n or Z represents a bond; R represents hydrogen, alkyl or alkylcarbonyl, R1 and R2 independently represent hydrogen or alkyl; or R1 and R2 together represent a C2-7 polymethylene chain; R3 represents hydrogen, hydroxy, alkoxy or acyloxy; R4 is hydrogen; R5 is hydrogen or R4 and R5 together represent a bond; R6 represents hydrogen, substituted or unsubstituted alkyl, alkoxy, C3-8 cycloalkyl, hydroxy, nitro, cyano, halo, formyl, carboxy, a group of formula RaT1-, RbRcNT-, RaT2NH-, RdCO.O-, RdCS.O-, Rd(OH)CH-, Rd(SH)CH-, RdC(=N.OH)-, RdC(=N.NH2)- or alkenyl optionally substituted by alkylcarbonyl, nitro or cyano; when Y represents CR7, R7 is independently selected from the variables mentioned above in relation to R6 providing that at least one of R6 or R7 is other than hydrogen; Ra represents Rd or RdO- and Rd represents substituted or unsubstituted alkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, optional substituents for Rd being up to 3 substituents selected from alkyl, alkoxy, hydroxy, halo, haloalkyl, nitro and cyano; Rb and Rc each independently represent hydrogen, alkyl or alkylcarbonyl; T represents a bond or T1, T1 represents -CS- or T2 and T2 represents -CO-, -SO- or -SO2- and R8 represents hydrogen, alkyl or substituted or unsubstituted aryl; R9 represents hydrogen or alkyl, substituted or unsubstituted aryl or R8 and R9 together represent a C3-7 polymethylene group; and n represents 0, 1 or 2; a process for preparing such a compound, a pharmaceutical composition containing such a compound and the use of such a compound or composition in medicine.(FR) Est décrit un composé ayant la formule (I) ou, selon le cas, un sel, un ester ou un amide de celui-ci utilisable par l'industrie pharmaceutique ou encore un solvate de celui-ci acceptable par l'industrie pharmaceutique, où X représente O ou S; Y représente N ou N+-O- ou une fraction de molécules CR7 où R7 est défini comme ci-après; Z est O, CH2, NR, S(O)n ou une liaison; R représente l'hydrogène, l'alkyle ou l'alkylcarbonyle, R1 et R2 représentent indépendamment l'hydrogène ou l'alkyle; ou R1 et R2 représentent ensemble une chaîne polyméthylène C2-7; R3 représente l'hydrogène, l'hydroxy, l'alkoxy ou l'acyloxy; R4 est l'hydrogène; R5 est l'hydrogène ou R4 et R5 représentent ensemble une liaison; R6 représente l'hydrogène, et substitués ou non, de l'alkyle, de l'alkoxy, du cycloalkyle C3-8, de l'hydroxy, du nitro, du cyano, du halo, du formyle, du carboxy, un groupe ayant pour formule RaT1-, RbRcNT-, RaT2NH-, RdCO.O-, RdCS.O-, Rd(OH)CH-, Rd(SH)CH-, RdC(=N.OH)-, RdC(=N.NH2)- ou un alkényle éventuellement substitué par de l'alkylcarbonyle, du nitro ou du cyano; quand Y représente CR7, R7 est sélectionné indépendamment parmi les variables mentionnées ci-avant relativement à R6, à condition qu'au moins une des molécules R6 ou R7 ne soit pas de l'hydrogène; Ra représente Rd ou RdO- et Rd représente un alkyle ou aryle ou un hétéroaryle substitués ou non, les substituants éventuels pour Rd s'élevant à 3 sélectionnés parmi l'aryle, l'alkoxy, l'hydroxy, l'halo, l'haloalkyle, le nitro et le cyano; Rb et Rc représentent chacun indépendamment l'hydrogène, l'alkyle ou l'alkylcarbonyle; T représente une liaison ou T1, T1 représente -CS- ou T2 et T2 représente -CO-, -SO- ou -SO2- et R8 représente l'hydrogène, l'alkyle et l'aryle substitué ou non; R9 représente l'hydrogène ou l'alkyle, l'aryle substitué ou non, ou bien R8 et R9 représentent ensemble un groupe polyméthylène C3-7; et n représente 0, 1 ou 2; procédé pour préparer un tel composé, ou composition pharmaceutique contenant un tel composé et utilisation d'un tel composé ou d'une telle composition en médecine.