4-(dimethylamino)benzylisocyanate | 99067-96-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(dimethylamino)benzylisocyanate
• 英文别名: 4-isocyanatomethyl-N,N-dimethyl-aniline；4-Isocyanatomethyl-N,N-dimethyl-anilin；4-(isocyanatomethyl)-N,N-dimethylaniline
• CAS: 99067-96-6
• 化学式: C₁₀H₁₂N₂O
• mdl: MFCD11593156
• 分子量: 176.218
• InChiKey: DOQROBBHWLBKLG-UHFFFAOYSA-N

物化性质

• 熔点：
  24.5-25 °C (sublm)
• 沸点：
  119 °C(Press: 4 Torr)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(dimethylamino)benzylisocyanate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 1-(4-(dimethylamino)benzyl)-4-(1-(4-methoxybenzyl)-5-amino-1H-imidazol-4-yl)-5-imino-1H-imidazol-2(5H)-one
  参考文献：
  名称：

  Structure-based drug design and potent anti-cancer activity of tricyclic 5:7:5-fused diimidazo[4,5-d:4′,5′-f][1,3]diazepines

  摘要：

  Judicial structural modifications of 5: 7-fused ring-expanded nucleosides (RENs), based on molecular modeling studies with one of its known targets, human RNA helicase (hDDX3), led to the lead, novel, 5:7-5-fused tricyclic heterocycle (1). The latter exhibited promising broad-spectrum in vitro anti-cancer activity against a number of cancer cell lines screened. This paper describes our systematic, albeit limited, structure-activity relationship (SAR) studies on this lead compound, which produced a number of analogs with broad-spectrum in vitro anti-cancer activities against lung, breast, prostate, and ovarian cancer cell lines, in particular compounds 15i, 15j, 15m and 15n which showed IC50 values in submicromolar to micromolar range, and are worthy of further explorations. The SAR data also enabled us to propose a tentative SAR model for future SAR efforts for ultimate realization of optimally active and minimally toxic anti-cancer compounds based on the diimidazo[4,5-d:4',5'-f][1,3]diazepine structural skeleton of the lead compound 1. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.050
• 作为产物：
  描述：

  4-dimethylaminobenzeneacetic acid methyl ester 在 硫酸 、 一水合肼 、 sodium nitrite 作用下， 反应 2.0h， 生成 4-(dimethylamino)benzylisocyanate
  参考文献：
  名称：

  Monosized macroporous resins with epoxy groups and their structure and gel chromatography properties

  摘要：

  The monosized macroporous-polymer beads based on cross-linked poly(glycidyl methacrylate) have been synthesized by a new improving method-combining dispersion polymerization with swelling polymerization and polymeric solution porogens. The structure and gel chromatographic properties of the resins have been studied. The resins as matrix materials of various types of high performance liquid chromatography (HPLC) packings possess excellent separation properties.

  DOI：

  10.1007/bf02884676

文献信息

• [EN] "TRPV1 VANILLOID RECEPTOR ANTAGONISTS WITH A BICYCLIC PORTION"<br/>[FR] ANTAGONISTES DU RÉCEPTEUR VANILLOÏDE TRPV1 AYANT UNE PARTIE BICYCLIQUE
  申请人：PHARMESTE SRL

  公开号：WO2011120604A1

  公开（公告）日：2011-10-06

  The invention discloses compounds of formula I wherein Y is a group of formula A, B, C, D, or E: and W, Q, n, R1, R2, R3, U1-U5, J and K have the meanings given in the description. The compounds of formula I are TRPV1 antagonists and are useful as active ingredients of pharmaceutical compositions for the treatment of pain and other conditions ameliorated by the inhibition of the vanilloid receptor TRPV1.

  该发明揭示了公式I的化合物，其中Y是公式A、B、C、D或E的一个基团；W、Q、n、R1、R2、R3、U1-U5、J和K具有描述中给出的含义。公式I的化合物是TRPV1拮抗剂，可用作药物组合物的活性成分，用于治疗通过抑制辣椒素受体TRPV1而改善的疼痛和其他病症。
• TRPV1 vanilloid receptor antagonists with a bicyclic portion
  申请人：Pharmeste S.r.l.

  公开号：EP2377850A1

  公开（公告）日：2011-10-19

  The invention discloses compounds of formula I wherein Y s selected from a group of formula and W, Q, n, R1, R2, R3, U1-U5 have the meanings given in the description. The compounds of formula I are TRPV1 antagonists and are useful as active ingredients of pharmaceutical compositions for the treatment of pain and other conditions ameliorated by the inhibition of the vanilloid receptor TRPV1. 1.

  该发明揭示了以下式的化合物： 其中Y选自以下式的一组 而W、Q、n、R1、R2、R3、U1-U5的含义如描述中所给出。 该式化合物是TRPV1拮抗剂，可用作药物组合物的活性成分，用于治疗疼痛和其他通过抑制辣椒素受体TRPV1而改善的症状。
• Design, Synthesis and Anticancer Activity of a New Series of N-aryl-N′-[4-(pyridin-2-ylmethoxy)benzyl]urea Derivatives
  作者：Shicheng Hou、Shishao Liang、Chao Zhang、Yingmei Han、Jianhui Liang、Hongyu Hu、Xingeng Zhang、Chun Hu、Xiaoping Liu、Hong Zhang

  DOI：10.3390/molecules26123496

  日期：——

  The development of cancer treatments requires continuous exploration and improvement, in which the discovery of new drugs for the treatment of cancer is still an important pathway. In this study, based on the molecular hybridization strategy, a new structural framework with an N-aryl-N’-arylmethylurea scaffold was designed, and 16 new target compounds were synthesized and evaluated for their antiproliferative

  癌症治疗的发展需要不断探索和改进，其中发现治疗癌症的新药仍然是重要途径。在这项研究中，基于分子杂交策略，一个新的结构框架与N-芳基-N设计了'-芳甲基脲支架，合成了16个新的目标化合物，并评估了它们对四种不同癌细胞系A549、MCF7、HCT116、PC3和人肝正常细胞系HL7702的抗增殖活性。结果表明，具有 1-methylpiperidin-4-yl 基团的 7 种化合物对所有四种癌细胞系都具有优异的活性，并且它们对 HL7702 几乎没有任何活性。其中，化合物9b和9d对4种细胞均表现出极好的活性，对MCF7和PC3细胞系的IC 50甚至小于3μM。
• Quinazolines as MMP-13 inhibitors
  申请人：——

  公开号：US20020193377A1

  公开（公告）日：2002-12-19

  A compound selected from those of formula (I): 1 in which: R 1 represents a group selected from hydrogen, amino, alkyl, alkenyl, aminoalkyl, aryl, arylalkyl, heterocycle, and cycloalkylalkyl, optionally substituted, W represents oxygen, sulfhur, or ═N—R′, in which R′ is as defined in the description, X 1 , X 2 and X 3 represent nitrogen or —C—R 6 in which R 6 is as defined in the description, Y represents oxygen, sulfhur, —NH, or —N(C 1 -C 6 )alkyl, Z represents oxygen, sulfhur, —NR 7 in which R 7 is as defined in the description, and 59 optionally carbon atom, n is an integer from 1 to 8 inclusive, Z 1 represents —CR 8 R 9 wherein R 8 and R 9 are as defined in the description, A represents aromatic or non-aromatic, heterocyclic or non-heterocyclic ring system, m is an integer from 0 to 7 inclusive, the group(s) R 2 is (are) is as defined in the description, R 3 represents hydrogen, alkyl, alkenyl, alkynyl, ot a group of formula: 2 in which Z 2 , B, R 5 , P and q are as defined in the description, optionally, the racemic forms thereof, isomers thereof, N-oxydes thereof, and the pharmaceutically acceptable salts thereof, and medicinal products containing the same are useful as specific inhibitors of type-13 matrix metalloprotease.

  从以下化学式（I）中选择的一种化合物： 其中： R1代表从氢、氨基、烷基、烯基、氨基烷基、芳基、芳基烷基、杂环和环烷基烷基中选择的基团，可选择取代； W代表氧、硫或═N—R′，其中R′如描述中定义； X1、X2和X3代表氮或—C—R6，其中R6如描述中定义； Y代表氧、硫、—NH或—N（C1-C6）烷基； Z代表氧、硫、—NR7，其中R7如描述中定义，且可选地是碳原子； n为1到8之间的整数； Z1代表—CR8R9，其中R8和R9如描述中定义； A代表芳香或非芳香、杂环或非杂环环系统； m为0到7之间的整数； R2代表如描述中定义的基团； R3代表氢、烷基、烯基、炔基或化学式2中的基团： 其中Z2、B、R5、P和q如描述中定义； 可选地，它们的外消旋体、异构体、N-氧化物和药学上可接受的盐，以及含有它们的药物制剂，可用作特异性抑制剂13型基质金属蛋白酶。
• Self-Sorting in Rodlike Micelles of Chiral Bisurea Bolaamphiphiles
  作者：Asish Pal、Pol Besenius、Rint P. Sijbesma

  DOI：10.1021/ja205345e

  日期：2011.8.24

  We have demonstrated the formation of segregated enantiomeric dynamic rods in water, from the self-sorting of chiral trans-1,2-bisureido cyclohexane-based bolaamphiphiles. Fluorescence probes have been used to investigate the self-sorting through forming exciplex and FRET.

  我们已经证明了在水中形成分离的对映体动态棒，来自手性反式-1,2-双脲基环己烷基双亲分子的自分选。荧光探针已被用于通过形成激基复合物和 FRET 来研究自分选。