3,5-双(甲氧基羰基)异氰酸苯酯 | 46828-05-1

• 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: 3,5-双(甲氧基羰基)异氰酸苯酯
• 中文别名: 5-异氰酸基异邻苯二甲酸二甲酯
• 英文名称: dimethyl 5-isocyanatoisophthalate
• 英文别名: dimethyl 5-isocyanatobenzene-1,3-dicarboxylate
• CAS: 46828-05-1
• 化学式: C₁₁H₉NO₅
• 分子量: 235.196
• InChiKey: JHCYWIFFIHXGAG-UHFFFAOYSA-N

物化性质

• 熔点：
  106-109 °C(lit.)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  82
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S22,S26,S36/37/39,S45
• 危险类别码：
  R20/22,R36/37/38,R42
• 海关编码：
  2929109000
• 储存条件：
  保持贮藏器密封，并将其放入一个紧密封装的容器中。储存时应选择阴凉、干燥的地方。

反应信息

• 作为反应物：
  描述：

  3,5-双(甲氧基羰基)异氰酸苯酯 在 氨 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 120.0h， 生成 5-[(3-Benzyloxy-2-pyridyl)carbamoylamino]benzene-1,3-dicarboxamide
  参考文献：
  名称：

  Structure-Based Design, Synthesis, and Biological Evaluation of Novel Inhibitors of Human Cyclophilin A

  摘要：

  Cyclophilin A is involved in many cellular processes, including protein folding and intracellular transports. Because cyclophilin A has been shown to interact with HIV-1 gag proteins and to enhance the viral infectivity, nonimmunosuppressive cyclophilin A ligands may represent a new class of therapeutic agents against HIV. Here, we report a virtual screening using structure- and pharmacophore-based design to identify original nonpeptidic cyclophilin ligands. Following a lead identification of compounds 1 [1-(3-benzyloxypyridin-2-yl)-3-(3-chlorophenyl)urea] and 2 [1-(3-benzyloxypyridin-2-yl)-3-(3-trifluoromethylphenyl)urea] (IC50 = 0.3 mu M), a series of molecules were synthesized from a diarylurea scaffold and evaluated for their in vitro ability to inhibit the cis-trans isomerase activity of cyclophilin A. Molecular modifications provided several more potent compounds, in particular analogues 4d and 4i with IC50 of 14 and 20 nM, respectively. Then, we evaluated the effect of analogues 1 and 2 on HIV virion infectivity in both immortalized and primary cells. Both 1 and 2 reduced virion infectivity in the replication-defective one-round infection assay, but only 1 impaired wild-type HIV infection in human peripheral blood mononuclear cells.

  DOI：

  10.1021/jm050716a
• 作为产物：
  描述：

  5-硝基间苯二甲酸二甲酯 在 盐酸 、 铁粉 、 乙酸乙酯 作用下， 生成 3,5-双(甲氧基羰基)异氰酸苯酯
  参考文献：
  名称：

  Acetals of polyhydric alcohols

  摘要：

  公开号：

  US02680730A1

文献信息

• Discovery of 14-3-3 Protein-Protein Interaction Inhibitors that Sensitize Multidrug-Resistant Cancer Cells to Doxorubicin and the Akt Inhibitor GSK690693
  作者：Mattia Mori、Giulia Vignaroli、Ylenia Cau、Jelena Dinić、Richard Hill、Matteo Rossi、David Colecchia、Milica Pešić、Wolfgang Link、Mario Chiariello、Christian Ottmann、Maurizio Botta

  DOI：10.1002/cmdc.201400044

  日期：2014.5

  synthesis, image‐based high‐content analysis of reporter cells, and in vitro assays using cancer cells. Notably, the two most active compounds promoted the translocation of c‐Abl and FOXO pro‐apoptotic factors into the nucleus and sensitized multidrug‐resistant cancer cells to apoptotic inducers such as doxorubicin and the pan‐Akt inhibitor GSK690693, thus becoming valuable lead candidates for further optimization

  14-3-3是一类高度保守的衔接蛋白，在药物化学家中引起了极大的兴趣。对14-3-3蛋白-蛋白质相互作用（PPI）的小分子抑制剂的需求量很大，既可以作为工具来增进我们对人类疾病中14-3-3的作用的了解，又可以开发创新的治疗药物。在此，我们通过多学科策略结合分子建模，有机合成，基于图像的报告细胞高含量分析以及使用癌细胞的体外测定方法，提出了新型14-3-3 PPI抑制剂的发现。值得注意的是，两种活性最高的化合物促进c-Abl和FOXO促凋亡因子向核内转移，并使对多药耐药的癌细胞向凋亡诱导剂（如阿霉素和pan-Akt抑制剂GSK690693）敏感，因此成为进一步优化的有价值的潜在候选人。我们的结果强调了14-3-3 PPI抑制剂在抗癌联合疗法中的可能作用。
• An automated, polymer-assisted strategy for the preparation of urea and thiourea derivatives of 15-membered azalides as potential antimalarial chemotherapeutics
  作者：Antun Hutinec、Renata Rupčić、Dinko Žiher、Kirsten S. Smith、Wilbur Milhous、William Ellis、Colin Ohrt、Zrinka Ivezić Schönfeld

  DOI：10.1016/j.bmc.2011.01.030

  日期：2011.3

  series of 15-membered azalide urea and thiourea derivatives has been synthesized and evaluated for their in vitro antimalarial activity against chloroquine-sensitive (D6), chloroquine/pyremethamine resistant (W2) and multidrug resistant (TM91C235) strains of Plasmodium falciparum. We have developed an effective automated synthetic strategy for the rapid synthesis of urea/thiourea libraries of a macrolide

  合成了一系列15元氮杂内酰胺脲和硫脲衍生物，并评估了它们对恶性疟原虫的氯喹敏感性（D6），氯喹/乙胺嘧啶抗性（W2）和多药耐药性（TM91C235）菌株的体外抗疟活性。我们已经开发出一种有效的自动化合成策略，用于大环内酯支架的尿素/硫脲库的快速合成。使用溶液相策略合成化合物，总收率为50–80％。大多数合成的化合物具有抑制作用。前三种化合物对所有三种菌株的效力比阿奇霉素高30-65倍，阿奇霉素具有抗疟疾活性。
• Design of chiral urea-quaternary ammonium salt hybrid catalysts for asymmetric reactions of glycine Schiff bases
  作者：Maximilian Tiffner、Johanna Novacek、Alfonso Busillo、Katharina Gratzer、Antonio Massa、Mario Waser

  DOI：10.1039/c5ra14466c

  日期：——

  Bifunctional chiral urea-containing quaternary ammonium salts can be straightforwardly synthesised and systematically fine-tuned for asymmetric reactions of glycine Schiff bases.

  含有尿素的双功能手性季铵盐可以直接合成，并经系统调整用于甘氨酸席夫碱的不对称反应。
• COMPOUNDS FOR THE TREATMENT OF ALZHEIMER'S DISEASE
  申请人：Fuchs Klaus

  公开号：US20100144681A1

  公开（公告）日：2010-06-10

  The invention relates to substituted 1,2-ethylenediamines of general formula (I), wherein the radicals R 1 -R 13 , A, B, L and i are as defined in the description and the claims. The invention also relates to the use thereof for treating Alzheimer's disease (AD) and similar diseases.

  该发明涉及一般式(I)的取代1,2-乙二胺化合物，其中基团R1-R13、A、B、L和i如描述和权利要求中所定义。该发明还涉及将其用于治疗阿尔茨海默病（AD）和类似疾病。
• Nickel/Photoredox-Catalyzed Amidation via Alkylsilicates and Isocyanates
  作者：Shuai Zheng、David N. Primer、Gary A. Molander

  DOI：10.1021/acscatal.7b02795

  日期：2017.11.3

  A nickel/photoredox, dual-catalyzed amidation reaction between alkylsilicate reagents and alkyl/aryl isocyanates is reported. In contrast to the previously reported reductive coupling process, this protocol is characterized by mild reaction conditions and the absence of a stoichiometric reductant. A mechanistic hypothesis involving a nickel-isocyanate adduct is proposed based on literature precedent

  报道了烷基硅酸酯试剂与烷基/芳基异氰酸酯之间的镍/光氧化还原双催化酰胺化反应。与先前报道的还原偶联过程相反，该方案的特征在于反应条件温和且不存在化学计量的还原剂。基于文献的先例并通过实验结果进一步验证，提出了一种涉及异氰酸镍加合物的机理假说。