p-aminocinnamic acid hydrochloride | 139223-62-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: p-aminocinnamic acid hydrochloride
• 英文别名: 4-aminocinnamic acid hydrochloride；3-(4-aminophenyl)-acrylic acid hydrochloride；(E)-3-(4-aminophenyl)prop-2-enoic acid;hydron;chloride
• CAS: 139223-62-4
• 化学式: C₉H₁₀NO₂*Cl
• 分子量: 199.637
• InChiKey: SFRAURMUQMJLPG-ZIKNSQGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  p-aminocinnamic acid hydrochloride 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成 3-(4-氨基苯基)丙酸
  参考文献：
  名称：

  HKGreen-3: A Rhodol-Based Fluorescent Probe for Peroxynitrite

  摘要：

  A novel fluorescent probe, HKGreen-3, for sensing peroxynitrite is designed on the basis of the rhodol scaffold and a peroxynitrite-specific oxidation reaction. The probe turns out to be highly sensitive and selective for detecting peroxynitrite in both chemical and biological systems.

  DOI：

  10.1021/ol102182j

文献信息

• Novel thiophene derivatives, their process of preparation and the pharmaceutical compositions which comprise them
  申请人：——

  公开号：US20040072871A1

  公开（公告）日：2004-04-15

  A compound of formula (I) selected from: 1 wherein: X represents oxygen or sulphur, Y represents oxygen, —NH— or —N(C 1 -C 6 )alkyl-, R a represents hydrogen, halogen, (C 1 -C 3 )alkyl, hydroxyl or (C 1 -C 3 )alkoxy, R b represents hydrogen, halogen or (C 1 -C 3 )alkyl, A represents phenyl, pyridyl, (C 5 -C 6 )cycloalkyl or (C 5 -C 6 )cycloalkenyl, R 1 and R 2 each represent a group selected from hydrogen, halogen, cyano, nitro, haloalkyl, haloalkoxy, alkyl, alkenyl, alkynyl, —OR 4 , —NR 4 R 5 , —S(O) n R 4 , —C(O)R 4 , —CO 2 R 4 , —O—C(O)R 4 , —C(O)NR 4 R 5 , —NR 5 —C(O)R 4 , —NR 5 —SO 2 R 4 , -T-CN, -T-OR 4 , -T-OCF 3 , -T- NR 4 R 5 , -T-S(O) n R 4 , -T-C(O)R 4 , -T-CO 2 R 4 , -T-O—C(O)R 4 , -T-C(O)NR 4 R 5 , -T-NR 4 —C(O)R 5 , -T-NR 4 —SO 2 R 5 , —R 6 and -T-R 6 in which n, T, R 4 , R 5 and R 6 are as defined in the description, R 3 represents an —R 7 or —U—R 11 group in which R 7 represents hydrogen, alkyl, aryl, cycloalkyl or heterocycle, U represents a linear or branched alkylene chain and R 11 is defined in the description, their optical isomers or their addition salts with a pharmaceutically acceptable acid or base, and their use as inhibitor of metalloproteinase and more specifically of metalloproteinase-12.

  公式（I）所选的化合物如下： 其中： X代表氧或硫， Y代表氧，-NH-或-N（C1-C6）烷基-， Ra代表氢，卤素，（C1-C3）烷基，羟基或（C1-C3）甲氧基， Rb代表氢，卤素或（C1-C3）烷基， A代表苯基，吡啶基，（C5-C6）环烷基或（C5-C6）环烯基， R1和R2分别代表从氢，卤素，氰基，硝基，卤代烷基，卤代甲氧基，烷基，烯基，炔基，-OR4，-NR4R5，-S（O）nR4，-C（O）R4，-CO2R4，-O—C（O）R4，-C（O）NR4R5，-NR5—C（O）R4，-NR5—SO2R4，-T-CN，-T-OR4，-T-OCF3，-T-NR4R5，-T-S（O）nR4，-T-C（O）R4，-T-CO2R4，-T-O—C（O）R4，-T-C（O）NR4R5，-T-NR4—C（O）R5，-T-NR4—SO2R5，-R6和-T-R6中选择的基团，其中n，T，R4，R5和R6如描述中所定义， R3代表-R7或-U-R11基团，其中R7代表氢，烷基，芳基，环烷基或杂环烷基，U代表线性或支链烷基链，R11如描述中所定义， 它们的光学异构体或它们与药学上可接受的酸或碱形成的加合盐，以及它们作为金属蛋白酶抑制剂，更具体地是金属蛋白酶-12的抑制剂的用途。
• Carbamic acid compounds comprising a sulfonamide linkage as hdac inhibitors
  申请人：——

  公开号：US20040077726A1

  公开（公告）日：2004-04-22

  This invention pertains to certain active carbamic acid compounds which inhibit HDAC activity and which have the following formula: (I) A is an aryl group; Q1 is a covalent bond or an aryl leader group; J is a sulfonamide linkage selected from: —S (═O)2NR1— and —NR1S(═O)2—; R1 is a sulfonamido substituent; and, Q2 is an acid leader group; with the proviso that if J is —S(═O)2NR1—, then Q1 is an aryl leader group; and pharmaceutically acceptable salts, solvates, amides, esters, ethers, chemically protected forms, and prodrugs thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit HDAC, and, e.g., to inhibit proliferative conditions, such as cancer and psoriasis.

  这项发明涉及抑制HDAC活性的某些活性碳酸酯化合物，其化学式如下：(I) A为芳基；Q1为共价键或芳基引导基团；J为从以下选取的磺胺酰胺连接：—S(═O)2NR1—和—NR1S(═O)2—；R1为磺胺基取代基；Q2为酸引导基团；但条件是如果J为—S(═O)2NR1—，则Q1为芳基引导基团；以及其药学上可接受的盐、溶剂化合物、酰胺、酯、醚、化学保护形式和前药。本发明还涉及包含这种化合物的药物组合物，以及在体内外使用这种化合物和组合物来抑制HDAC，例如抑制增殖性疾病，如癌症和牛皮癣。
• Discovery of Aminopyridine-Based Inhibitors of Bacterial Enoyl-ACP Reductase (FabI)
  作者：William H. Miller、Mark A. Seefeld、Kenneth A. Newlander、Irene N. Uzinskas、Walter J. Burgess、Dirk A. Heerding、Catherine C. K. Yuan、Martha S. Head、David J. Payne、Stephen F. Rittenhouse、Terrance D. Moore、Stewart C. Pearson、Valerie Berry、Walter E. DeWolf、Paul M. Keller、Brian J. Polizzi、Xiayang Qiu、Cheryl A. Janson、William F. Huffman

  DOI：10.1021/jm020050+

  日期：2002.7.1

  inhibitor of FabI from S. aureus (IC(50) = 2.4 microM) and Haemophilus influenzae (IC(50) = 4.2 microM). Compound 9 has good in vitro antibacterial activity against several organisms, including S. aureus (MIC = 0.5 microg/mL), and is effective in vivo in a S. aureus groin abscess infection model in rats. Through FabI overexpressor and macromolecular synthesis studies, the mode of action of 9 has been confirmed

  细菌烯酰-ACP还原酶（FabI）催化细菌脂肪酸生物合成的每个循环中的最后一步，是开发新型抗菌剂的有吸引力的目标。我们鉴定有效的选择性FabI抑制剂的努力始于对GlaxoSmithKline专有化合物的筛选，该鉴定了几种金黄色葡萄球菌FabI的小分子抑制剂。通过结合迭代化学化学和基于X射线晶体结构的设计，将这些引线之一开发为新型氨基吡啶衍生物9，一种来自金黄色葡萄球菌（IC（50）= 2.4 microM）和嗜血杆菌的低微摩尔FabI抑制剂。流感（IC（50）= 4.2 microM）。化合物9对包括金黄色葡萄球菌（MIC = 0.5 microg / mL）在内的几种生物具有良好的体外抗菌活性，并且在S. 大鼠金黄色腹股沟脓肿感染模型。通过FabI过表达子和大分子合成研究，已证实9的作用方式是通过抑制FabI来抑制脂肪酸生物合成。综上所述，这些结果支持FabI作为有效的抗菌靶标，并证明了
• Tuning Second-Order Optical Nonlinearities in Push-Pull Benzimidazoles
  作者：Antonio Carella、Roberto Centore、Alain Fort、Andrea Peluso、Augusto Sirigu、Angela Tuzi

  DOI：10.1002/ejoc.200300786

  日期：2004.6

  characterization of new chromophores with second order optical nonlinearities containing the 2-phenyl-(5,6)-nitrobenzimidazole group is reported. Starting from 2-4-[(4-N,N-dihydroxyethylamino)phenylazo]phenyl}-5(6)-nitrobenzimidazole, a combined theoretical and experimental approach, including theoretical computations of second order nonlinear optical activity (MNDO/AM1), X-ray structural analysis and

  报道了含有 2-苯基-(5,6)-硝基苯并咪唑基团的具有二阶光学非线性的新型发色团的合成和完整表征。从 2-4-[(4-N,N-dihydroxyethylamino)phenylazo]phenyl}-5(6)-nitrobenzimidazole 开始，一种理论和实验相结合的方法，包括二阶非线性光学活性 (MNDO/AM1) 的理论计算X 射线结构分析和合成策略导致相关发色团 NLO 活性的显着优化（超过 50%）。结果表明，6-硝基取代的化合物比5-硝基取代的化合物更具活性，并且通过在苯并咪唑和2-苯环之间插入碳-碳双键可以进一步提高NLO活性。计算还表明，在用吸电子基团对 6-硝基苯并咪唑的 N1 原子进行功能化后，非线性度会进一步改善。测量了 940 和 1550 之间的实验非线性（EFISH 技术，μβ/10−48 esu，λ = 1.907 μm，DMF 溶液）。(© Wiley-VCH
• Substituted anilides
  申请人：Aventis Pharma Limited

  公开号：US06479519B1

  公开（公告）日：2002-11-12

  The invention is directed to physiologically active compounds of formula (I): wherein: R1 is hydrogen, halogen, hydroxy, lower alkyl or lower alkoxy; X1, X2 and X6 independently represent N or CR10; and one of X3, X4 and X5 represents CR11 and the others independently represents N or CR10; where R10 is hydrogen, amino, halogen, hydroxy, lower alkyl, lower alkoxy, lower alkylthio, lower alkylsulphinyl, lower alkylsulphonyl, nitro or trifluoromethyl; and R11 represents a group —L1—Ar1—L2—Y; and the corresponding N-oxides, and their prodrugs; and pharmaceutically acceptable salts and solvates of such compounds and their N-oxides and prodrugs. Such compounds have valuable pharmaceutical properties, in particular the ability to regulate the interaction of VCAM-1 and fibronectin with the integrin VLA-4 (&agr;4&bgr;1).

  该发明涉及公式（I）的生理活性化合物： 其中： R1是氢，卤素，羟基，较低烷基或较低烷氧基； X1，X2和X6独立地表示N或CR10; 而X3、X4和X5中的一个表示CR11，其他的独立地表示N或CR10； 其中，R10是氢，氨基，卤素，羟基，较低烷基，较低烷氧基，较低烷基硫基，较低烷基亚砜基，较低烷基磺酰基，硝基或三氟甲基； R11表示一个基团—L1—Ar1—L2—Y； 以及这些化合物的相应N-氧化物、它们的前药；和这些化合物及它们的N-氧化物和前药的药学上可接受的盐和溶剂。这些化合物具有有价值的药物特性，特别是调节VCAM-1和纤维连接蛋白与整合素VLA-4（α4β1）相互作用的能力。