3-(4-羟基苯基)丙-2-烯腈 | 82628-73-7

• 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-羟基苯基)丙-2-烯腈
• 英文名称: trans-4-hydroxyphenylacrilonitrile
• 英文别名: (E)-3-(4-hydroxyphenyl)acrylonitrile；4-hydroxy-trans-cinnamonitrile；1-cyano-2-(4-hydroxyphenyl)ethylene；p-Hydroxycinnamonitrile；(E)-3-(4-hydroxyphenyl)prop-2-enenitrile
• CAS: 82628-73-7
• 化学式: C₉H₇NO
• 分子量: 145.161
• InChiKey: RZROIDXECXAOTO-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-羟基苯基)丙-2-烯腈 、 D-半胱氨酸盐酸盐 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以8%的产率得到(4S)-2-[(E)-2-(4-hydroxyphenyl)ethenyl]-4,5-dihydro-1,3-thiazole-4-carboxylic acid
  参考文献：
  名称：

  开发简单的萤火虫萤光素类似物，发出蓝，绿，红和近红外生物窗口光

  摘要：

  开发了发出蓝，绿和红光的简单萤火虫萤光素类似物。在675 nm处观察到最长的最大发射，属于NIR生物窗口（650-900 nm），可用于活体动物的深部生物成像。与天然荧光素的快速发射相比，类似物显示出发射强度的缓慢上升。与类似物本身相比，腺苷酸化类似物的发光大大增强。

  DOI：

  10.1016/j.tet.2013.03.050
• 作为产物：
  描述：

  4-甲氧基烟腈 在 三溴化硼 作用下， 以20%的产率得到3-(4-羟基苯基)丙-2-烯腈
  参考文献：
  名称：

  Tyrphostins I: synthesis and biological activity of protein tyrosine kinase inhibitors

  摘要：

  A novel class of low molecular weight protein tyrosine kinase inhibitors is described. These compounds constitute a systematic series of molecules with a progressive increase in affinity toward the substrate site of the EGF receptor kinase domain. These competitive inhibitors also effectively block the EGF-dependent autophosphorylation of the receptor. The potent EGF receptor kinase blockers examined were found to competitively inhibit the homologous insulin receptor kinase at 10(2)-10(3) higher inhibitor concentrations in spite of the significant homology between these protein tyrosine kinases. These results demonstrate the ability to synthesize selective tyrosine kinase inhibitors. The most potent EGF receptor kinase inhibitors also inhibit the EGF-dependent proliferation of A431/clone 15 cells with little or no effect on EGF independent cell growth. These results demonstrate the potential use of protein tyrosine kinase inhibitors as selective antiproliferative agents for proliferative diseases caused by the hyperactivity of protein tyrosine kinases. We have suggested the name "tyrphostins" for this class of antiproliferative compounds which act as protein tyrosine kinase blockers.

  DOI：

  10.1021/jm00130a020

文献信息

• Inhibition of intestinal apical membrane Na/phosphate co-transportation in humans
  申请人：——

  公开号：US20030162753A1

  公开（公告）日：2003-08-28

  The compounds of formula (I) are hydrophilic aryl phosphate, thiophosphate, and aminophosphate intestinal apical membrane Na-mediated phosphate co-transportation inhibitors. The compounds can be administered orally, where they act to inhibit Na-dependent phosphate uptake in the intestines, or internally, where they interact with the phosphate control functions of the kidneys and parathyroid. They are useful for inhibiting sodium-mediated phosphate uptake, reducing serum PTH, calcium, calcitriol, and phosphate, and treating renal disease in an animal, including a human.

  化合物的化学式（I）为亲水性芳基磷酸酯、硫代磷酸酯和氨基磷酸酯，是肠道顶端膜Na介导的磷酸盐共同运输抑制剂。这些化合物可以经口服给药，在肠道中起到抑制Na依赖性磷酸盐摄取的作用，或者内部给药，在肾脏和甲状旁腺的磷酸盐控制功能中发挥作用。它们可用于抑制钠介导的磷酸盐摄取，降低血清PTH、钙、钙三醇和磷酸盐，治疗动物（包括人类）的肾脏疾病。
• Small molecule perimeter defense in entomopathogenic bacteria
  作者：Jason M. Crawford、Cyril Portmann、Xu Zhang、Maarten B. J. Roeffaers、Jon Clardy

  DOI：10.1073/pnas.1201160109

  日期：2012.7.3

  Two Gram-negative insect pathogens, Xenorhabdus nematophila and Photorhabdus luminescens , produce rhabduscin, an amidoglycosyl- and vinyl-isonitrile-functionalized tyrosine derivative. Heterologous expression of the rhabduscin pathway in Escherichia coli , precursor-directed biosynthesis of rhabduscin analogs, biochemical assays, and visualization using both stimulated Raman scattering and confocal fluorescence microscopy established rhabduscin’s role as a potent nanomolar-level inhibitor of phenoloxidase, a key component of the insect’s innate immune system, as well as rhabduscin’s localization at the bacterial cell surface. Stimulated Raman scattering microscopy visualized rhabduscin at the periphery of wild-type X. nematophila cells and E. coli cells heterologously expressing the rhabduscin pathway. Precursor-directed biosynthesis created rhabduscin mimics in X. nematophila pathway mutants that could be accessed at the bacterial cell surface by an extracellular bioorthogonal probe, as judged by confocal fluorescence microscopy. Biochemical assays using both wild-type and mutant X. nematophila cells showed that rhabduscin was necessary and sufficient for potent inhibition (low nM) of phenoloxidases, the enzymes responsible for producing melanin (the hard black polymer insects generate to seal off microbial pathogens). These observations suggest a model in which rhabduscin’s physical association at the bacterial cell surface provides a highly effective inhibitor concentration directly at the site of phenoloxidase contact. This class of molecules is not limited to insect pathogens, as the human pathogen Vibrio cholerae also encodes rhabduscin’s aglycone, and bacterial cell-coated immunosuppressants could be a general strategy to combat host defenses.

  两种革兰氏阴性昆虫病原菌，Xenorhabdus nematophila和Photorhabdus luminescens，产生拉布杜斯辛（rhabduscin），这是一种含有氨基糖苷和乙烯基异腈基化的酪氨酸衍生物。通过在大肠杆菌Escherichia coli中异源表达拉布杜斯辛途径，预体定向生物合成拉布杜斯辛类似物，生化分析以及使用受激拉曼散射和共聚焦荧光显微镜进行可视化，确定了拉布杜斯辛在昆虫先天免疫系统的关键组成部分苯氧化酶中作为有效的纳摩尔级抑制剂的作用，以及拉布杜斯辛在细菌细胞表面的定位。受激拉曼散射显微镜可视化了野生型X. nematophila细胞和异源表达拉布杜斯辛途径的E. coli细胞周边的拉布杜斯辛。预体定向生物合成在X. nematophila途径突变体中创建了拉布杜斯辛模拟物，这些模拟物可以通过胞外生物正交探针在细菌细胞表面访问，如共聚焦荧光显微镜所示。使用野生型和突变型X. nematophila细胞的生化分析表明，拉布杜斯辛对于产生黑色聚合物（昆虫用于封闭微生物病原体的硬质黑色聚合物）的酶苯氧化酶的强效抑制（低纳摩尔级）是必要且充分的。这些观察结果表明，拉布杜斯辛在细菌细胞表面的物理结合提供了直接在苯氧化酶接触点处高效抑制剂浓度的模型。这类分子不仅限于昆虫病原体，因为人类病原体Vibrio cholerae也编码了拉布杜斯辛的无糖基骨架，而且细菌细胞包覆的免疫抑制剂可能是对抗宿主防御的一般策略。
• [EN] VINYL ISOCYANIDE COMPOUNDS AS ANTIBACTERIAL AGENTS<br/>[FR] COMPOSÉS DE VINYLE ISOCYANURE UTILISÉS EN TANT QU'AGENTS ANTIBACTÉRIENS
  申请人：UNIV BATH

  公开号：WO2022238694A1

  公开（公告）日：2022-11-17

  Compounds of formula (I) or formula (II) are disclosed: Wherein Y1, Y2, and Y3are independently selected from C-R1or N. Such compounds find use as antibiotics and antifungals.

  公开了化学式(I)或化学式(II)的化合物：其中Y1、Y2和Y3独立地选自C-R1或N。这些化合物可用作抗生素和抗真菌剂。
• Antifungal azole compounds
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0174769A1

  公开（公告）日：1986-03-19

  1,3-Diazolyl-2-propanol derivatives of the formula:- wherein X and Y are N or CH, R' is phenyl, heterocyclyl, heterocyclyl-alkyl, -alkenyl or - alkynyl, optionally substituted, R2 and R3 are hydrogen or alkyl, and R4 and R5 are hydrogen, amino, alkoxyalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, or alkenyl, or phenyl, phenylalkyl or phenylalkenyl, heterocycyl, heterocyclylalkyl or heterocyclylalkenyl, each optionally substituted, provided that when R1 is optionally substituted phenyl at least one of R1, R4 and R5 is, or contains, a phenyl ring bearing at least one substituent selected from cyano, cyanoalkyl, nitro, aminocarbonylalkyl, halogenoalkoxy and radicals of the formulae -CONR6R7, -NHCOR8 or OR9 as defined herein, and the acid addition salts of compounds which contain a basic substituent; together with processes for their manufacture, pharmaceutical, veterinary and plant antifungal compositions, a method of treating fungal diseases in plants, and the use of the compounds for the manufacture of pharmaceutical or veterinary antifungal compositions.

  式中的 1，3-二氮唑-2-丙醇衍生物：- 1，3-二氮唑-2-丙醇衍生物 其中X和Y是N或CH，R'是任选取代的苯基、杂环基、杂环烷基、-烯基或-炔基，R2和R3是氢或烷基，R4和R5是氢、氨基、烷氧基烷基、氨基烷基、烷基氨基烷基、二烷基氨基烷基、或烯基、或苯基、苯基烷基或苯基烯基、杂环基、杂环烷基或杂环烷基，各自任选取代、条件是当 R1 是任选取代的苯基时，R1、R4 和 R5 中至少有一个是或含有一个苯基环，该苯基环上至少有一个取代基，该取代基可选自氰基、氰基烷基、硝基、氨基羰基烷基、卤代烷氧基和本文定义的-CONR6R7、-NHCOR8 或 OR9 式中的基团，以及含有碱性取代基的化合物的酸加成盐；连同其生产工艺、药用、兽用和植物抗真菌组合物、治疗植物真菌疾病的方法，以及使用这些化合物生产药用或兽用抗真菌组合物。
• Cosmestic composition
  申请人：UNILEVER PLC

  公开号：EP0572167A1

  公开（公告）日：1993-12-01

  A composition suitable for topical application to mammalian skin and hair for inducing, maintaining or increasing hair growth comprises a hair growth promoter chosen from glutamic acid derivatives and salts thereof. The composition preferably also comprises an activity enhancer which may be chosen from hair growth stimulants, penetration enhancers and cationic polymers.

  一种适用于哺乳动物皮肤和毛发的外用组合物，可诱导、维持或增加毛发生长，其中包括一种毛发生长促进剂，选自谷氨酸衍生物及其盐类。该组合物最好还包含一种活性增强剂，它可以选自毛发生长刺激剂、渗透增强剂和阳离子聚合物。