1,1'-(3,5-dimethoxyphenyl)disulfide | 219696-68-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,1'-(3,5-dimethoxyphenyl)disulfide
• 英文别名: 1,2-bis(3,5-dimethoxyphenyl)disulfane；bis(3,5-dimethoxyphenyl)-disulfide；di-(3,5-dimethoxyphenyl) disulfide；Bis(3,5-dimethoxyphenyl)disulfide；1-[(3,5-dimethoxyphenyl)disulfanyl]-3,5-dimethoxybenzene
• CAS: 219696-68-1
• 化学式: C₁₆H₁₈O₄S₂
• 分子量: 338.449
• InChiKey: AGXICOQOLMPJIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  87.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,1'-(3,5-dimethoxyphenyl)disulfide 在 sodium hydride 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 methyl 5-chloro-3-[(3,5-dimethoxyphenyl)thio]-1H-indole-2-carboxylate
  参考文献：
  名称：

  New Arylthioindoles:  Potent Inhibitors of Tubulin Polymerization. 2. Structure−Activity Relationships and Molecular Modeling Studies

  摘要：

  Arylthioindoles (ATIs) that possess a 3-methoxyphenylthio or a 3,5-dimethoxyphenylthio moiety at position 2 of the indole ring were effective tubulin assembly inhibitors, but weak inhibitors of MCF-7 cell growth. ATIs bearing a 3-(3,4,5-trimethoxyphenyl)thio moiety were potent tubulin polymerization inhibitors, with IC(50)s in the 2.0 (35) to 4.5 (37) mu M range. They also inhibited MCF-7 cell growth at nanomolar concentrations. The 3,4,5-trimethoxy substituted ATIs showed potencies comparable to those of the reference compounds colchicine and combretastatin A-4 in both tubulin assembly and cell growth inhibition assays. Dynamics simulation studies correlate well with the observed experimental data. Furthermore, from careful analysis of the biological and in silico data, we can now hypothesize a basic pharmacophore for this class of compounds.

  DOI：

  10.1021/jm050809s
• 作为产物：
  描述：

  3,5-二甲氧基苯胺 在 盐酸 、 碘 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 0.92h， 生成 1,1'-(3,5-dimethoxyphenyl)disulfide
  参考文献：
  名称：

  New Arylthioindoles:  Potent Inhibitors of Tubulin Polymerization. 2. Structure−Activity Relationships and Molecular Modeling Studies

  摘要：

  Arylthioindoles (ATIs) that possess a 3-methoxyphenylthio or a 3,5-dimethoxyphenylthio moiety at position 2 of the indole ring were effective tubulin assembly inhibitors, but weak inhibitors of MCF-7 cell growth. ATIs bearing a 3-(3,4,5-trimethoxyphenyl)thio moiety were potent tubulin polymerization inhibitors, with IC(50)s in the 2.0 (35) to 4.5 (37) mu M range. They also inhibited MCF-7 cell growth at nanomolar concentrations. The 3,4,5-trimethoxy substituted ATIs showed potencies comparable to those of the reference compounds colchicine and combretastatin A-4 in both tubulin assembly and cell growth inhibition assays. Dynamics simulation studies correlate well with the observed experimental data. Furthermore, from careful analysis of the biological and in silico data, we can now hypothesize a basic pharmacophore for this class of compounds.

  DOI：

  10.1021/jm050809s

文献信息

• New Inhibitors of Indoleamine 2,3-Dioxygenase 1: Molecular Modeling Studies, Synthesis, and Biological Evaluation
  作者：Antonio Coluccia、Sara Passacantilli、Valeria Famiglini、Manuela Sabatino、Alexandros Patsilinakos、Rino Ragno、Carmela Mazzoccoli、Lorenza Sisinni、Alato Okuno、Osamu Takikawa、Romano Silvestri、Giuseppe La Regina

  DOI：10.1021/acs.jmedchem.6b00718

  日期：2016.11.10

  Indoleamine 2,3-dioxygenase 1 (IDO1) is an attractive target for anticancer therapy. Herein, we report a virtual screening study which led to the identification of compound 5 as a new IDO1 inhibitor. In order to improve the biological activity of the identified hit, arylthioindoles 6–30 were synthesized and tested. Among these, derivative 21 exhibited an IC50 value of 7 μM, being the most active compound

  吲哚胺 2,3-双加氧酶 1 (IDO1) 是抗癌治疗的一个有吸引力的目标。在此，我们报告了一项虚拟筛选研究，该研究导致将化合物5鉴定为新的 IDO1 抑制剂。为了提高所识别命中的生物活性，arylthioindoles 6 - 30合成并测试。其中，衍生物21的IC 50值为7 μM，是该系列中活性最强的化合物。此外，化合物5和21诱导表达 IDO1 的癌细胞系 HTC116 和 HT29 的剂量依赖性生长抑制。为了使获得的结果合理化并提出新的化学修饰，进行了三维定量构效关系研究。
• Copper-Catalyzed Cycloaddition of Heterobicyclic Alkenes with Diaryl Disulfides to Synthesize Dihydrobenzo[b]thiophene Derivatives
  作者：Qifu Lin、Wen Yang、Yongqi Yao、Yue Li、Lin Wang、Dingqiao Yang

  DOI：10.1021/acs.joc.0c03034

  日期：2021.3.5

  developed. The C—S and C—C bonds can be formed simultaneously on the C═C bond of the olefins via a single-step cycloaddition to afford a series of 2,3-dihydrobenzo[b]thiophene derivatives. This reaction exhibits excellent diastereoselectivity and relatively broad substrate scope. Various functional groups attached to the substrates are tolerated in this protocol to give the corresponding exo adducts in moderate

  已经开发了新颖的铜催化的二芳基二硫化物与杂环双环烯烃的环加成反应。可以通过单步环加成在烯烃的C═C键上同时形成CS和CC键，从而提供一系列2,3-二氢苯并[b]噻吩衍生物。该反应表现出优异的非对映选择性和相对宽的底物范围。在该方案中可以耐受与底物相连的各种官能团，从而以中等收率得到相应的外加合物。
• Tricyclic fused heterocycle compounds, process for preparing the same and use thereof
  申请人：Nippon Suisan Kaisha, Ltd.

  公开号：US06602898B1

  公开（公告）日：2003-08-05

  Compounds represented by formula (1), wherein X is, for example, CH, CH2, CHR (wherein R is a lower alkyl group or a substituted lower alkyl group) or CRR′ (wherein R and R′ are the same as the above defined R); Y is, for example, CH, CH2 or C═O; Z is, for example, O, S, S=O or SO2; U is C or N; R1 to R4 are each independently, for example, a hydrogen atom, OR, SR (wherein R is the same as defined above), or an aromatic ring, a substituted aromatic ring or a heterocycle; at least one of R5 and R8 is, for example, OH and the remaining of R5 and R8 are each independently, for example, a hydrogen atom or OH, optical isomers thereof, conjugates thereof or pharmaceutically acceptable salts thereof are provided. These compounds are characterized in having a wide range of pharmacological actions such as an excellent relaxing action of tracheal smooth muscles, an inhibition of airway hypersensitivity and an inhibition of infiltration of inflammatory cells into the airway and, in addition, high safety.

  由公式（1）表示的化合物，其中X是，例如，CH，CH2，CHR（其中R是较低的烷基或取代的较低烷基）或CRR′（其中R和R′与上述定义的R相同）；Y是，例如，CH，CH2或C═O；Z是，例如，O，S，S=O或SO2；U是C或N；R1至R4分别是，例如，氢原子，OR，SR（其中R与上述定义的相同），或芳香环，取代芳香环或杂环；R5和R8中的至少一个是，例如，OH，其余的R5和R8分别是，例如，氢原子或OH，其光学异构体，共轭物或药学上可接受的盐。这些化合物具有广泛的药理作用，例如优异的舒张气管平滑肌作用，抑制气道过敏和抑制炎症细胞进入气道，此外，具有高安全性。
• Process for producing dibenzo[b,f]thiepine derivatives
  申请人：Nippon Suisan Kaisha, Ltd.

  公开号：US06207837B1

  公开（公告）日：2001-03-27

  Efficient synthesis of diaryl sulfide derivatives useful as intermediates for pharmaceutical compounds. Provision of a convenient process for producing large quantities of dibenzo[b,f]thiepine derivatives using such intermediates. Halogen-substituted phenyl derivatives of the general formula (1): (where X is a halogen atom and R1-R5 is any substituent selected from among hydrogen, a lower alkyl group, a lower cycloalkyl group, an aryl group, a halogen atom, a lower alkoxyl group, an amino group, an N-lower acylamino group, a nitro group, a lower alkylthio group and a carboxyl group) are reacted with disulfide derivatives of the general formula (2): (where R6-R10 is any substituent selected from among hydrogen, a lower alkyl group, a lower cycloalkyl group, an aryl group, a halogen atom, a lower alkoxyl group, an amino group, an N-lower acylamino group, a nitro group, a lower alkylthio group and a carboxyl group) in the presence of metal catalysts to form a sulfide bond, thereby producing diaryl sulfide derivatives of the general formula (3): (where R1-R10 are the same as defined above) or salts thereof. Pharmaceutical compounds such as dibenzo[b,f]thiepine derivatives are produced from the diaryl sulfide derivatives or salts thereof by known techniques.

  高效合成二芳基硫醚衍生物，作为制药化合物的中间体。提供一种方便的方法，使用这些中间体生产大量的二苯并[b,f]噻吩衍生物。将一般式（1）中卤代苯衍生物（其中X为卤素原子，R1-R5是从氢、低碳基、低环烷基、芳基、卤素原子、低烷氧基、氨基、N-低酰基氨基、硝基、低烷硫基和羧基中选择的任何取代基）与一般式（2）中的二硫化物衍生物（其中R6-R10是从氢、低碳基、低环烷基、芳基、卤素原子、低烷氧基、氨基、N-低酰基氨基、硝基、低烷硫基和羧基中选择的任何取代基）在金属催化剂存在下反应，形成硫醚键，从而产生一般式（3）中的二芳基硫醚衍生物（其中R1-R10与上述定义相同）或其盐。通过已知技术，可以从二芳基硫醚衍生物或其盐制备制药化合物，例如二苯并[b,f]噻吩衍生物。
• Single Atom Copper Catalyst for S-arylation Reaction to Produce Diaryl Disulfides
  作者：Yiming Zhao、Yan Zhou、Shanshan Lv、Han Li、Qikang Wu、Shaohuan Liu、Wanying Li、Taiyu Chen、Zheng Chen

  DOI：10.1039/d2sc06738b

  日期：——

  electronic or steric groups successfully realized S-arylation and produced the corresponding diaryl disulfides with high selectivity. The fully exposed single-atom Cu with flexible electronic characteristics successively realized oxidative addition or coordination of multiple substrates, making it possible to obtain diaryl disulfide with high selectivity.

  CeO x纳米棒催化剂(Cu 1 /CeO x )负载的单原子Cu通过端羟基在CeO x表面上的锚定合成。CeO x纳米棒的氧缺陷特性通过Ce-O-Cu界面促进Cu和CeO x之间的电子转移，实现了Cu位点的灵活电子调控。X射线光电子能谱、X射线精细结构能谱和电子顺磁共振能谱证实，形成了氧化态在+1和+2之间的单原子Cu物种。Cu 1 /CeO x在使用芳基碘化物的S-芳基化反应中，作为一种对元素硫具有先进催化性能的催化剂，实现了 97.1% 的碘苯转化率和 94.8% 的二苯基二硫化物选择性。具有不同电子或位阻基团的取代碘苯成功地实现了S-芳基化，并以高选择性生成了相应的二芳基二硫化物。充分暴露的具有柔性电子特性的单原子Cu，先后实现了多种底物的氧化加成或配位，从而有可能获得高选择性的二芳基二硫化物。