11-(3-Methylaminopropyl)-11H-dibenz-1,4-oxathiepin | 82387-10-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 11-(3-Methylaminopropyl)-11H-dibenz-1,4-oxathiepin
• 英文别名: UNC10100001A；11-(3-Methylaminopropyl)-11H-dibenz(b,f)-1,4-oxathiepin；3-(11h-Dibenzo[b,f][1,4]oxathiepin-11-yl)-n-methylpropan-1-amine；3-(6H-benzo[b][1,5]benzoxathiepin-6-yl)-N-methylpropan-1-amine
• CAS: 82387-10-8
• 化学式: C₁₇H₁₉NOS
• 分子量: 285.41
• InChiKey: OKHWNJARAFKRRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲氧基苯硫酚 在 氢氧化钾 、 sodium hydroxide 、 sodium dihydrogenphosphate 、 正丁基锂 、 氢溴酸 、 氯甲酸乙酯 、 铜 、 potassium carbonate 作用下， 以 乙醇 、 正己烷 、 乙酸酐 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 11-(3-Methylaminopropyl)-11H-dibenz-1,4-oxathiepin
  参考文献：
  名称：

  Tricyclic psychotropic agents containing two chalcogen atoms in the central ring: Derivatives of 11H-dibenz[b,f]-1,4-oxathiepin

  摘要：

  2-溴苄溴和其类似物XVII和XXV与2-羟基硫代苯酚的反应产生了11H-二苯[b,f]-1,4-噁硫杂环戊烷(Ia)及其2-氯(Ib)和2-三氟甲基衍生物(IC)。从Ia和Ib衍生的锂化合物与二氧化碳和二甲基氨基烷氯化物的处理得到化合物IIa、Va和VIab；侧链的改变导致胺类化合物IVa、VIIa和VIIIa。通过用亚硫酰氯或N-氯琥珀酰亚胺氯化物氯化化合物Ibc，然后用1-甲基-4-哌啶基氯化镁处理，得到11-(1-甲基-4-哌啶基)衍生物Xbc。化合物Ib经氧化转化为磺酮XX，经过与氢化钠和叔-氨基烷基氯化物处理得到基本磺酮XXI和XXII。核未取代的带有脂肪侧链的胺类化合物(IVa和VIIa)具有强烈的抗利血平活性，是潜在的抗抑郁药物，而骨架2位有取代基的11-(1-甲基-4-哌啶基)衍生物(Xbc)是潜在的神经阻滞剂；特别是三氟甲基衍生物Xc具有出色的猫病和抗阿波莫啡效果。

  DOI：

  10.1135/cccc19820967

文献信息

• METHODS AND COMPOUNDS FOR THE TREATMENT OF GENETIC DISEASE
  申请人：Design Therapeutics, Inc.

  公开号：US20210238226A1

  公开（公告）日：2021-08-05

  The present disclosure relates to compounds and methods for modulating the expression of dmpk, atxn1, atxn2, atxn3, cacna1a, atxn7, ppp2r2br tbp, htt, jph3r ar, or atn1 and treating diseases and conditions in which dmpk, atxn1, atxn2, atxn3, cacna1a, atxn1, ppp2r2b, tbp, htt, jph3, ar, or atn1 plays an active role. The compound can be a transcription modulator molecule having a first terminus, a second terminus, and oligomeric backbone, wherein: a) the first terminus comprises a DNA-binding moiety capable of noncovalently binding to a nucleotide repeat sequence CAG or CTG; b) the second terminus comprises a protein-binding moiety binding to a regulatory molecule that modulates an expression of a gene comprising the nucleotide repeat sequence CAG or CTG; and c) the oligomeric backbone comprising a linker between the first terminus and the second terminus.
• US4431808A
  申请人：——

  公开号：US4431808A

  公开（公告）日：1984-02-14
• Tricyclic psychotropic agents containing two chalcogen atoms in the central ring: Derivatives of 11H-dibenz[b,f]-1,4-oxathiepin
  作者：Karel Šindelář、Jiří Holubek、Miroslav Ryska、Antonín Dlabač、Jiřina Metyšová、Emil Svátek、Marta Hrubantová、Jiří Protiva、Miroslav Protiva

  DOI：10.1135/cccc19820967

  日期：——

  Reactions of 2-bromobenzyl bromide and its analogues XVII and XXV with 2-hydroxythiophenol resulted in 11H-dibenz[b,f]-1,4-oxathiepin (Ia) and its 2-chloro (Ib) and 2-trifluoromethyl derivative (IC). Treatment of the lithium compounds derived from Ia and Ib with carbon dioxide and dimethylaminoalkyl chlorides gave compounds IIa, Va and VIab; modification of side chains led to amines IVa, VIIa and VIIIa. 11-(1-Methyl-4-piperidyl) derivatives Xbc were obtained by chlorination of compounds Ibc with sulfuryl chloride or N-chlorosuccinimide and the following treatment with 1-methyl-4-piperidylmagnesium chloride. Compound Ib was transformed by oxidation to the sulfone XX affording by treatment with sodium hydride and tert-aminoalkylchlorides the basic sulfones XXI and XXII. While the nuclearly unsubstituted amines with the aliphatic side chains (IVa and VIIa) have intensive antireserpine activity and are potential antidepressants, the 11-(1-methyl-4-piperidyl) derivatives with a substituent in position 2 of the skeleton (Xbc) are potential neuroleptics; the trifluoromethyl derivative Xc especially has outstanding cataleptic and antiapomorphine efficacy.

  2-溴苄溴和其类似物XVII和XXV与2-羟基硫代苯酚的反应产生了11H-二苯[b,f]-1,4-噁硫杂环戊烷(Ia)及其2-氯(Ib)和2-三氟甲基衍生物(IC)。从Ia和Ib衍生的锂化合物与二氧化碳和二甲基氨基烷氯化物的处理得到化合物IIa、Va和VIab；侧链的改变导致胺类化合物IVa、VIIa和VIIIa。通过用亚硫酰氯或N-氯琥珀酰亚胺氯化物氯化化合物Ibc，然后用1-甲基-4-哌啶基氯化镁处理，得到11-(1-甲基-4-哌啶基)衍生物Xbc。化合物Ib经氧化转化为磺酮XX，经过与氢化钠和叔-氨基烷基氯化物处理得到基本磺酮XXI和XXII。核未取代的带有脂肪侧链的胺类化合物(IVa和VIIa)具有强烈的抗利血平活性，是潜在的抗抑郁药物，而骨架2位有取代基的11-(1-甲基-4-哌啶基)衍生物(Xbc)是潜在的神经阻滞剂；特别是三氟甲基衍生物Xc具有出色的猫病和抗阿波莫啡效果。