3,4-二甲氧基苄基异氰酸酯 | 14596-50-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,4-二甲氧基苄基异氰酸酯
• 英文名称: 3,4-dimethoxybenzyl isothiocyanate
• 英文别名: 3,4-dimethoxybenzylisothiocyanate；dMBITC；isothiocyanate；Veratryl-isothiocyanat；4-(isothiocyanatomethyl)-1,2-dimethoxybenzene
• CAS: 14596-50-0
• 化学式: C₁₀H₁₁NO₂S
• mdl: MFCD00060409
• 分子量: 209.269
• InChiKey: MTKPIGBIMQONMN-UHFFFAOYSA-N

物化性质

• 熔点：
  29-32°C
• 沸点：
  135-137 °C(Press: 0.3 Torr)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT-HARMFUL
• 危险类别码：
  R20/21/22,R36/37/38,R36/37/38:,R
• 危险品运输编号：
  UN 2811
• 海关编码：
  2930909090
• 安全说明：
  S26

反应信息

• 作为反应物：
  描述：

  3,4-二甲氧基苄基异氰酸酯 在 水 作用下， 生成 3,4-二甲氧基苄醇
  参考文献：
  名称：

  苯甲酸型异硫氰酸酯在加氢蒸馏模拟条件下的稳定性

  摘要：

  巴西五角大楼已知百伦（五叶科）含有苄基，3-甲氧基苄基，4-甲氧基苄基，3,4-二甲氧基苄基和吲哚型芥子油苷，从其根中获得的精油主要由异硫氰酸苄酯和苄基构成。氰化物。在作者的先前研究中，据推测，一种主要的预期化合物4-甲氧基苄基异硫氰酸酯的部分水解降解发生在精油制备的加氢蒸馏过程中。为了探究这一假设，选择了多种取代的苄基型异硫氰酸酯用于标准的加氢蒸馏模拟条件。用二氯甲烷萃取后，使用GC-MS分析反应混合物。液-液萃取得到的水相通过HPLC和GC-MS进行分析。2-甲氧基苄基

  DOI：

  10.1021/jf3041534
• 作为产物：
  描述：

  3,4-二甲氧基苄胺 在 双氧水 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 3,4-二甲氧基苄基异氰酸酯
  参考文献：
  名称：

  异硫氰酸酯作为微管蛋白聚合抑制剂的合成及构效关系研究

  摘要：

  在干扰微管形成过程的各种物质中，异硫氰酸盐（ITC）是一组其结合模式和作用机制尚未得到解释的化合物。为了更好地理解微管蛋白-异硫氰酸酯相互作用的构效关系，我们设计并合成了一系列16种已知的和新颖的、结构多样的ITC，包括氨基酸酯衍生的异硫氰酸酯、双异硫氰酸酯、异硫氰酸苄酯的类似物和磷类似物萝卜硫素。所有合成的化合物和选定的天然异硫氰酸酯（BITC、PEITC、AITC 和 SFN）均经过体外测试，以评估其抗增殖活性、微管蛋白聚合抑制潜力以及对细胞周期进程的影响。大多数新测试化合物的抗增殖活性超过了天然异硫氰酸酯的作用，其中四种结构作为微管蛋白聚合抑制剂比 BITC 更有效。作为抗微管蛋白活性的证实，对于最具活性的化合物，观察到聚合抑制与 G2/M 期细胞周期停滞之间的相关性。鉴于生物学结果表明结构多样的异硫氰酸酯对微管蛋白聚合的影响存在显着差异，因此进行了计算机分析以分析异硫氰酸酯-微管蛋

  DOI：

  10.3390/ijms241813674

文献信息

• Convenient Synthesis of 5-Arylidene-2-imino-4-thiazolidinone Derivatives Using Microwave Irradiation
  作者：Emmanuelle Braud、Manal Sarkis、Diem-Ngan Tran、Maria Dasso Lang、Christiane Garbay

  DOI：10.1055/s-0033-1341108

  日期：——

  A concise approach for the preparation of 5-arylidene-2-imino-4-thiazolidinone derivatives is described. Structurally diverse amines, isothiocyanates, aldehydes, and chloroacetyl chloride were combined under microwave irradiation to afford new 5-arylidene-2-imino-4-thiazolidinone derivatives. The one-pot synthesis involves the in situ formation of a thiourea followed by reaction with chloroacetyl chloride

  描述了一种用于制备 5-arylidene-2-imino-4-thiazolidinone 衍生物的简明方法。结构不同的胺、异硫氰酸酯、醛和氯乙酰氯在微波辐射下结合，得到新的 5-亚芳基-2-亚氨基-4-噻唑烷酮衍生物。一锅合成包括硫脲的原位形成，然后与氯乙酰氯和醛反应生成目标化合物。
• Nitrogen-containing heterocyclic compounds
  申请人：——

  公开号：US20020068734A1

  公开（公告）日：2002-06-06

  The present invention provides nitrogen-containing heterocyclic compounds and pharmaceutically acceptable salts thereof which inhibit phosphorylation of PDGF receptor to hinder abnormal cell growth and cell wandering and thus are useful for the prevention or treatment of cell-proliferative diseases such as arteriosclerosis, vascular reobstruction, cancer and glomerulosclerosis. The compounds are represented by general formula (I): 1 wherein V represents an oxygen atom or a sulfur atom; W represents 1,4-piperazinediyl or 1,4-homopiperazinediyl in which carbons on the ring may be substituted by unsubstituted alkyl groups; X represents a nitrogen atom or C-R 9 ; Y represents a nitrogen atom or C-R 8 ; Z represents a nitrogen atom or C-R 7 (provided that at least one of X, Y and Z represents a nitrogen atom); R 1 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic alkyl group, etc.; R 2 represents a substituted alkyl group, a substituted or unsubstituted alicyclic alkyl group, etc.; R 3 , R 4 , R 5 and R 6 , which may be the same or different, each represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a nitro group, a cyano group, OR 12 , —NR 15 R 16 , etc.; R 7 represents a halogen atom, etc.; R 8 has the same significance as R 7 , and R 9 represents a hydrogen atom or —COR 41 .

  本发明提供了含氮杂环化合物及其药学上可接受的盐，其抑制PDGF受体的磷酸化，以阻碍异常细胞生长和细胞游走，因此可用于预防或治疗细胞增殖性疾病，如动脉硬化、血管再狭窄、癌症和肾小球硬化。所述化合物由通式（I）表示：其中V表示氧原子或硫原子；W表示1,4-哌嗪基或1,4-同源哌嗪基，其中环上的碳可以被未取代的烷基取代；X表示氮原子或C-R9；Y表示氮原子或C-R8；Z表示氮原子或C-R7（前提是X、Y和Z中至少有一个表示氮原子）；R1表示氢原子、取代或未取代的烷基、取代或未取代的脂环烷基等；R2表示取代的烷基、取代或未取代的脂环烷基等；R3、R4、R5和R6，可以相同也可以不同，每个表示氢原子、卤素原子、取代或未取代的烷基、硝基、氰基、OR12、—NR15R16等；R7表示卤素原子等；R8具有与R7相同的意义，且R9表示氢原子或—COR41。
• NITROGENOUS HETEROCYCLIC COMPOUNDS
  申请人：KYOWA HAKKO KOGYO KABUSHIKI KAISHA

  公开号：EP0882717A1

  公开（公告）日：1998-12-09

  The present invention provides nitrogen-containing heterocyclic compounds and pharmaceutically acceptable salts thereof which inhibit phosphorylation of PDGF receptor to hinder abnormal cell growth and cell wandering and thus are useful for the prevention or treatment of cell-proliferative diseases such as arteriosclerosis, vascular reobstruction, cancer and glomerulosclerosis. The compounds are represented by general formula (I): wherein V represents an oxygen atom or a sulfur atom; W represents 1,4-piperazinediyl or 1,4-homopiperazinediyl in which carbons on the ring may be substituted by unsubstituted alkyl groups; X represents a nitrogen atom or C-R9; Y represents a nitrogen atom or C-R8; Z represents a nitrogen atom or C-R7 (provided that at least one of X, Y and Z represents a nitrogen atom); R1 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic alkyl group, etc.; R2 represents a substituted alkyl group, a substituted or unsubstituted alicyclic alkyl group, etc.; R3, R4, R5 and R6, which may be the same or different, each represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a nitro group, a cyano group, - OR12, -NR15R16, etc.; R7 represents a halogen atom, etc.; R8 has the same significance as R7, and R9 represents a hydrogen atom or -COR41.

  本发明提供了含氮杂环化合物及其药学上可接受的盐类，它们能抑制 PDGF 受体的磷酸化，从而阻碍细胞的异常生长和游走，因此可用于预防或治疗细胞增殖性疾病，如动脉硬化、血管再阻塞、癌症和肾小球硬化症。这些化合物由通式 (I) 表示： 其中 V 代表氧原子或硫原子； W 代表 1,4-哌嗪二基或 1,4-高哌嗪二基，其中环上的碳可被未取代的烷基取代； X 代表氮原子或 C-R9； Y 代表氮原子或 C-R8 Z 代表氮原子或 C-R7（条件是 X、Y 和 Z 中至少有一个代表氮原子）； R1 代表氢原子、取代或未取代的烷基、取代或未取代的脂环烷基等； R2 代表取代的烷基、取代或未取代的脂环烷基等； R3、R4、R5 和 R6 可以相同或不同，各自代表氢原子、卤素原子、取代或未取代的烷基、硝基、氰基、- OR12、-NR15R16 等； R7 代表卤素原子等； R8 与 R7 意义相同，以及 R9 代表氢原子或-COR41。
• Potent and Selective Inhibitors of PDGF Receptor Phosphorylation. 2. Synthesis, Structure Activity Relationship, Improvement of Aqueous Solubility, and Biological Effects of 4-[4-(<i>N</i>-Substituted (thio)carbamoyl)-1-piperazinyl]-6,7-dimethoxyquinazoline Derivatives
  作者：Kenji Matsuno、Takao Nakajima、Michio Ichimura、Neill A. Giese、Jin-Chen Yu、Nathalie A. Lokker、Junko Ushiki、Shin-ichi Ide、Shoji Oda、Yuji Nomoto

  DOI：10.1021/jm0201114

  日期：2002.9.1

  4-[4-(N-Substituted(thio)carbamoyl)-1-piperazinyl]-6,7-dimethoxyquinazoline derivatives such as KN1022 are potent inhibitors of the phosphorylation of platelet derived growth factor receptor (PDGFR). Structure activity relationships in the (thio)urea moiety, the phenyl ring itself, the linker between these two moieties, and the piperazine moiety were investigated. The role of the linker was found to be quite different, where ureas yielded decreasing activity, while thioureas provided increasing activity. Cyanoguanidine as a bioisostere of thiourea and related dicyanovinyl or nitrovinyl groups were not suitable for potent activity. A hydrogen atom on the (thio)urea moiety was essential for activity. Stereochemistry was also important for inhibition of PDGFR phosphorylation. Through the modification of these moieties, benzylthiourea analogues with a small substituent on the 4-position and the 3,4-methylenedioxy group (KN734/CT52923) were found to be optimal for selective and potent activity. Replacement of the phenyl ring by heterocycles improved aqueous solubility without loss of activity and kinase selectivity. Introduction of a methyl group on 5-position of the piperazine ring and replacement by homopiperazine reduced inhibitory activity. An efficient synthetic method was also developed for 2-pyridylurea-containing analogues, via carbonylation of 2-aminopyridine with N,N'-carbonyldiimidazole. A potent analogue, KN734, inhibited smooth muscle cell proliferation and migration induced by platelet derived growth factor-BB (PDGF-BB) and suppressed neointima formation following balloon injury in rat carotid artery by oral administration. Therefore, 4-[4(N-substituted (thio)carbamoyl)-1-piperazinyl]-6,7-dimethoxyquinazoline derivatives may be expected to have potential as therapeutic agents for the treatment of restenosis.
• The First Potent Inhibitors for Human Glutaminyl Cyclase:  Synthesis and Structure−Activity Relationship
  作者：Mirko Buchholz、Ulrich Heiser、Stephan Schilling、André J. Niestroj、Katrin Zunkel、Hans-Ulrich Demuth

  DOI：10.1021/jm050756e

  日期：2006.1.1

  The first effective inhibitors for human glutaminyl cyclase (QC) are described. The structures are developed by applying a ligand-based optimization approach starting from imidazole. Screening of derivatives of that heterocycle led to compounds of the imidazol-1-yl-alkyl thiourea type as a lead scaffold. A library of thiourea derivatives was synthesized, resulting in an inhibitory improvement by 2 orders of magnitude, leading to 1-(3-(1H-imidazol-1-yl)propyl)-3-(3,4-dimethoxyphenyl)thiourea as a potent inhibitor. Systematic exploitation of the scaffold revealed a strong impact on the inhibitory efficacy and resulted in the development of imidazole-propyl-thioamides as another new class of potent inhibitors. A flexible alignment of the most potent compounds of the thioamide and thiourea class and a QC substrate revealed a good match of characteristic features of the molecules, which suggests a similar binding mode of both inhibitors and the substrate to the active site of QC.

表征谱图