2-溴-1-[4-(4-氯苯基)苯基]乙酮 | 613-34-3

• 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: 2-溴-1-[4-(4-氯苯基)苯基]乙酮
• 英文名称: 1-(4-(4-chlorophenyl)phenyl)-2-bromoethan-1-one
• 英文别名: 4-(4'-chlorophenyl)bromoacetophenone；1-(2-Bromoethanone)-4-(4-chloro-phenyl)-benzene；2-bromo-4'-(p-chlorophenyl)acetophenone；2-bromo-1-(4'-chloro-biphenyl-4-yl)-ethanone；2-bromo-1-(4'-chloro[1,1'-biphenyl]-4-yl)-ethanone；2-Brom-1-(4'-chlor-biphenyl-4-yl)-aethanon；2-Bromo-1-[4-(4-chlorophenyl)phenyl]ethanone
• CAS: 613-34-3
• 化学式: C₁₄H₁₀BrClO
• 分子量: 309.59
• InChiKey: VEZSDYKJTTXNDS-UHFFFAOYSA-N

物化性质

• 熔点：
  125-127 °C
• 沸点：
  395.5±22.0 °C(Predicted)
• 密度：
  1.464±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-溴-1-[4-(4-氯苯基)苯基]乙酮 在 三氯化铝 、 五氯化磷 、 四丁基碘化铵 、 borane tert-butylamine 、 sodium sulfite 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 26.0h， 生成 4-chloro-biphenylethanesulfonyl chloride
  参考文献：
  名称：

  Tetrahydroisoquinoline-3-carboxylate based matrix-metalloproteinase inhibitors: design, synthesis and structure–activity relationship

  摘要：

  The design, synthesis and structure-activity relationship (SAR) of a series of nonpeptidic 2-arylsulfonyl-1,2,3,4-tetra-hydro-isoquinoline-3-carboxylates and-hydroxamates as inhibitors of the matrix metalloproteinase human neutrophil collagenase (MMP-8) is described here. Based on available X-ray structures of MMP-8/inhibitor complexes, our structure-based design strategy was directed to complement major protein-ligand interaction regions mainly in the S1' hydrophobic specificity pocket close to the catalytic zinc ion. Here, the rigid 1,2,3,4-tetrahydroisoquinoline scaffold (Tic) provides ideal geometry to combine hydroxamates and carboxylates as typical zinc complexing functionalities, with a broad variety of S1' directed mono- and biaryl substituents consisting of aromatic rings perfectly accommodated within this more hydrophobic region of the MMP-8 inhibitor binding site. The effect of different S1' directed substituents, zinc-complexing groups, chirality and variations of the tetrahydroisoquinoline ring-system is investigated by systematic studies. X-ray structure analyses in combination with 3D-QSAR studies provided an additional understanding of key determinants for MMP-8 affinity in this series. The hypothetical binding mode for a typical molecule as basis for our inhibitor design was found in good agreement with a 1.7 Angstrom X-ray structure of this candidate in complex with the catalytic domain of human MMP-8. After analysis of all systematic variations, 3D-QSAR and X-ray structure analysis, novel S1' directed substituents were designed and synthesized and biologically evaluated. This finally results in inhibitors, which do not only show high biological affinity for MMP-8, but also exhibit good oral bioavailability in several animal species. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00215-8
• 作为产物：
  描述：

  1-(4'-氯-联苯-4-基)-乙酮 在 溴 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以65%的产率得到2-溴-1-[4-(4-氯苯基)苯基]乙酮
  参考文献：
  名称：

  具有抗氧化剂和角鲨烯合酶抑制活性的降脂（杂）芳族四氢-1,4-恶嗪衍生物。

  摘要：

  发现许多新合成的2- [4-（杂）芳基]苯基-2-羟基-四氢-1,4-恶嗪衍生物和大鼠角鲨烯均抑制脂质过氧化（最有效的IC50为20 microM）。合酶（IC50多数在1-10 microM之间）。在体内已证明了抗血脂异常的作用：最有效的化合物以56 micromol / kg（ip）的剂量将高脂血症大鼠的甘油三酸酯，总胆固醇和LDL-胆固醇分别降低了64％，67％和82％。大多数新型化合物比结构上相关的和参考的联苯吗啉具有更高的活性，这为抗动脉粥样硬化剂的设计提供了有用的结构方法。

  DOI：

  10.1021/jm800663w

文献信息

• Substituted cycloalkanecarboxylic acid derivatives as matrix
  申请人：Bayer Corporation

  公开号：US05886022A1

  公开（公告）日：1999-03-23

  Inhibitors for matrix metalloproteases, pharmaceutical compositions containing them, and a process for using them to treat a variety of physiological conditions. The compounds of the invention have the generalized formula ##STR1## wherein each T is a substituent g roup; x is 0, 1, or 2; the group D represents ##STR2## the subscript "e" is 2 or 3; the group R.sup.14 represents a variety of possible substituent groups of the cycloalkyl ring between D and G; the subscript "k" is 0-2; and the group G represents M, ##STR3## in which M represents --CO.sub.2 H, --CON(R.sup.11).sub.2, or --CO.sub.2 R.sup.12 ; and R.sup.13 represents any of the side chains of the 19 noncyclic occurring amino acids.

  抑制基质金属蛋白酶的抑制剂，含有它们的药物组合物，以及使用它们治疗各种生理状况的方法。该发明的化合物具有一般化学式##STR1##其中每个T是一个取代基团；x为0、1或2；D代表##STR2##下标"e"为2或3；R.sup.14代表D和G之间的环烷基环上可能的各种取代基团；下标"k"为0-2；G代表M，##STR3##其中M代表--CO.sub.2 H，--CON(R.sup.11).sub.2，或--CO.sub.2 R.sup.12；R.sup.13代表19种非环状氨基酸的任何一个侧链。
• Use of substituted 4-biarylbutyric and 5-biarylpentanoic acid derivatives as matrix metalloprotease inhibitors for the treatment of respiratory diseases
  申请人：Fitzgerald Mary F.

  公开号：US06900194B1

  公开（公告）日：2005-05-31

  Novel 4-Biarylbutyric and 5-Biarylpentanoic Acid Derivatives, use of substituted 4-Biarylbutyric and 5-Biarylpentanoic Acid Derivatives as Matrix Metalloprotease Inhibitors for the Treatment of Respiratory Diseases, pharmaceutical compositions containing them, and a process for using them. The compounds of the invention have the generalized formula (I) (T) x A—B—D—E—CO 2 H wherein A is an aryl or heteroaryl rings; B is an aryl or heteroaryl ring or a bond; each T is a substituent group, x is 0, 1, or 2; the group D represents (a), (b), (c), or (d); the group E represents a two or three carbon chain bearing one to three substituent groups which are independent or are involved in ring formation, possible structures being shown in the text and claims; and each of the substituents on E is an independent substituent; and include pharmaceutically acceptable salts thereof.

  新型4-联苯丁酸和5-联苯戊酸衍生物，以取代的4-联苯丁酸和5-联苯戊酸衍生物作为基质金属蛋白酶抑制剂用于治疗呼吸道疾病，含有它们的药物组合物，以及使用它们的方法。发明的化合物具有广义式（I）（T）x A—B—D—E—CO2H，其中A是芳基或杂环芳基环；B是芳基或杂环芳基环或键；每个T是取代基，x为0、1或2；D代表（a）、（b）、（c）或（d）；E代表一个带有一个到三个取代基的两个或三个碳链，这些取代基是独立的或参与环形成，可能的结构在文本和权利要求中显示；E上的每个取代基都是独立的取代基；并包括其药用盐。
• SUBSTITUTED TETRAHYDROISOQUINOLINES USED IN THE FORM OF MMP INHIBITORS, METHOD FOR THE PRODUCTION AND USE THEREOF IN THE FORM OF DRUGS
  申请人：Hofmeister Armin

  公开号：US20070203118A1

  公开（公告）日：2007-08-30

  The present invention is directed to a compound of formula (I) wherein R 1 , R 2 , R 3 , R 4 , A, L and n are as defined herein, or a pharmacologically acceptable salt thereof, its pharmaceutical composition and it use as a MMP inhibitor.

  本发明涉及一种具有以下化学式(I)的化合物，其中R1、R2、R3、R4、A、L和n如本文所定义，或其药理学上可接受的盐，以及其药物组合物及其作为MMP抑制剂的用途。
• Method of treating diabetes mellitus using arylglyoxals
  申请人：American Cyanamid Company

  公开号：US04536517A1

  公开（公告）日：1985-08-20

  A method of treating diabetes mellitus using arylglyoxals which are known compounds.

  使用已知化合物芳基乙二醛治疗糖尿病的方法。
• Derivatives of substituted 4-biarylbutyric acid as matrix
  申请人：Bayer Corporation

  公开号：US05789434A1

  公开（公告）日：1998-08-04

  Inhibitors for matrix metalloproteases, pharmaceutical compositions containing them, and a process for using them to treat a variety of physiological conditions. The presently claimed compounds have the generalized formula ##STR1## in which each T represents a substituent group; x is 0, 1, or 2; D represents ##STR2## .delta. is 0 or 1; U' represents O, S, or N, with the proviso that when U' is N, then .delta.=0, and when U' is O or S, then .delta.=1; R.sup.14 is any of a variety of substituent groups; and G represents M, ##STR3## in which M represents --CO.sub.2 H, --CON(R.sup.11).sub.2, or --CO.sub.2 R.sup.12, R.sup.11 represents H or an alkyl group, R.sup.12 represents an alkyl group, and R.sup.13 represents any of the side chains of the 19 noncyclic naturally occurring amino acids; and pharmaceutically acceptable salts thereof.

  抑制基质金属蛋白酶的抑制剂，含有它们的药物组合物，以及使用它们治疗各种生理状况的方法。目前所宣称的化合物具有一般化学式##STR1##其中每个T代表一个取代基团；x为0、1或2；D代表##STR2##.delta.为0或1；U'代表O、S或N，但当U'为N时，.delta.=0，当U'为O或S时，.delta.=1；R14代表各种取代基团之一；G代表M，##STR3##其中M代表--CO2H，--CON(R11)2或--CO2R12，R11代表H或烷基基团，R12代表烷基基团，R13代表19种非环状天然氨基酸的任何一个侧链；及其药用盐。