methyl 2-([1,1'-biphenyl]-4-yl)-2-bromoacetate | 169884-54-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-([1,1'-biphenyl]-4-yl)-2-bromoacetate
• 英文别名: Biphenyl-4-yl-bromo-acetic acid methyl ester；methyl 2-bromo-2-(4-phenylphenyl)acetate
• CAS: 169884-54-2
• 化学式: C₁₅H₁₃BrO₂
• 分子量: 305.171
• InChiKey: UYPNJQUYZCUWQE-UHFFFAOYSA-N

物化性质

• 沸点：
  380.4±30.0 °C(Predicted)
• 密度：
  1.378±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 2-([1,1'-biphenyl]-4-yl)-2-bromoacetate 在 sodium hydroxide 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 60.0h， 生成 2-([1,1'-biphenyl]-4-yl)acrylic acid
  参考文献：
  名称：

  Toward an Optimal Joint Recognition of the S₁‘ Subsites of Endothelin Converting Enzyme-1 (ECE-1), Angiotensin Converting Enzyme (ACE), and Neutral Endopeptidase (NEP)

  摘要：

  The formation of vasoconstrictors (e.g., angiotensin II and endothelin) and the inactivation of vasodilators (e.g., bradykinin and atrial natriuretic) by membrane-bound zinc metallopeptidases are key mechanisms in the control of blood pressure and fluid homeostasis. The way in which these peptides modulate physiological functions has been intensively studied. With the aim to develop compounds that can jointly block the three metallopeptidases-neutral endopeptidase (NEP, neprilysin), angiotensin-converting enzyme (ACE), and endothelin-converting enzyme (ECE-1)-we studied the common structural specificity of the S-1' subsites of these peptidases. Various mercaptoacyl amino acids of the general formula HS-CH2-CH(R-1')CO-Trp-OH, possessing more or less constrained R-1' side chains, were designed. The mercapto-acyl synthons contain one or two asymmetrical centers. The K-i values of the separated stereoisomers of the most efficient inhibitors were used to determine the stereochemical preference of each enzyme. A guideline for the joint inhibition of the three peptidases was obtained with the (2R,3R) isomer of compound 13b. Its K-i values on NEP, ACE, and ECE were 0.7, 43, and 26 nM, respectively.

  DOI：

  10.1021/jm0005454
• 作为产物：
  描述：

  4-联苯乙酸 在 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 7.0h， 生成 methyl 2-([1,1'-biphenyl]-4-yl)-2-bromoacetate
  参考文献：
  名称：

  在光氧化还原催化下生成碳正离子：用1-氟烷基苄基溴进行亲电芳香取代

  摘要：

  在温和的条件下，建立了芳烃的新型弗里德-克来福特型烷基化反应，以制得有价值的1-氟烷基-1,1-联芳基化合物。成功的关键是借助可见光光氧化还原催化，通过两个连续的单电子转移过程，高效生成不稳定的苄基碳正离子中间体。这种独特的活化方式避免了在传统的Friedel-Crafts反应中生成不稳定的碳正离子所需的强路易斯酸和高温。该协议证明了光灭活催化电子失活的苄基C-Br键杂合形成不稳定碳正离子中间体的第一个例子。

  DOI：

  10.1021/acs.orglett.0c03258

文献信息

• Novel Benzoxazine and Benzothiazine Derivatives as Multifunctional Antihyperlipidemic Agents
  作者：Alexios N. Matralis、Maria G. Katselou、Anastasios Nikitakis、Angeliki P. Kourounakis

  DOI：10.1021/jm200763k

  日期：2011.8.11

  in its manifestation. To address this disorder, we applied a strategy involving the design of a single chemical compound able to simultaneously modulate more than one target. We hereby present the development of novel benzoxazine and benzothiazine derivatives that significantly inhibit in vitro microsomal lipid peroxidation and LDL oxidation as well as squalene synthase activity (IC50 of 5–16 μM). Further

  动脉粥样硬化是一种多因素疾病，多种机制参与其表现。为了解决这种疾病，我们采用了一种策略，该策略涉及设计一种能够同时调节多个目标的单一化合物。我们在此提出了新型苯并恶嗪和苯并噻嗪衍生物的开发，这些衍生物显着抑制了体外微粒体脂质过氧化和LDL氧化以及角鲨烯合酶的活性（IC 50（5-16μM）。此外，这些化合物在体内显示出抗血脂异常和抗氧化特性，使高脂血症大鼠的总胆固醇，LDL，甘油三酸酯和MDA含量降低26-74％。最后，通过确定其在靶组织（血液/肝脏）中的体内浓度（长达24小时），表明化合物可以在低微摩尔范围内达到其靶标。对于开发用于治疗动脉粥样硬化的疾病改良剂的新药效基团，新化合物似乎是有趣的多功能分子。
• Therapeutic methods and compounds
  申请人：Ampio Pharmaceuticals, Inc.

  公开号：US09522893B2

  公开（公告）日：2016-12-20

  The invention provides diketopiperazines of formula I. The invention also provides pharmaceutical compositions comprising the diketopiperazines, or pharmaceutically-acceptable salts or prodrugs thereof, as the active ingredient. The invention further provides therapeutic treatments that utilize the diketopiperazines of formula I, including inhibition of a proliferative disease or condition, inhibition of angiogenesis, treatment of an angiogenic disease or condition, treatment of cancer and precancerous conditions, treatment of a fibrotic disorder, treatment of a viral infection, treatment of an Akt-mediated disease or condition, inhibition of the production, release or both of matrix metalloproteinase-9, and inhibition of Akt activation.

  该发明提供了式I的二酮哌啶。该发明还提供了包含该二酮哌啶的药物组合物，或其药用盐或前药作为活性成分。该发明还提供了利用式I的二酮哌啶进行的治疗方法，包括抑制增殖性疾病或状况，抑制血管生成，治疗血管生成性疾病或状况，治疗癌症和癌前病变，治疗纤维化疾病，治疗病毒感染，治疗Akt介导的疾病或状况，抑制基质金属蛋白酶-9的产生、释放或两者，以及抑制Akt的激活。
• Therapeutic Methods and Compounds
  申请人：Bar-Or David

  公开号：US20100105698A1

  公开（公告）日：2010-04-29

  The invention provides diketopiperazines of formula I. The invention also provides pharmaceutical compositions comprising the diketopiperazines, or pharmaceutically-acceptable salts or prodrugs thereof, as the active ingredient. The invention further provides therapeutic treatments that utilize the diketopiperazines of formula I, including inhibition of a proliferative disease or condition, inhibition of angiogenesis, treatment of an angiogenic disease or condition, treatment of cancer and precancerous conditions, treatment of a fibrotic disorder, treatment of a viral infection, treatment of an Akt-mediated disease or condition, inhibition of the production, release or both of matrix metalloproteinase-9, and inhibition of Akt activation.

  本发明提供了式I的二酮肽。本发明还提供包含该二酮肽或其药学上可接受的盐或前药物的制药组合物作为活性成分。本发明进一步提供了利用式I的二酮肽的治疗方法，包括抑制增殖性疾病或状况，抑制血管生成，治疗血管生成性疾病或状况，治疗癌症和癌前病变，治疗纤维化疾病，治疗病毒感染，治疗Akt介导的疾病或状况，抑制基质金属蛋白酶-9的产生、释放或两者，以及抑制Akt的激活。
• THERAPEUTIC METHODS AND COMPOUNDS
  申请人：Bar-Or David

  公开号：US20120157473A1

  公开（公告）日：2012-06-21

  The invention provides diketopiperazines of formula I. The invention also provides pharmaceutical compositions comprising the diketopiperazines, or pharmaceutically-acceptable salts or prodrugs thereof, as the active ingredient. The invention further provides therapeutic treatments that utilize the diketopiperazines of formula I, including inhibition of a proliferative disease or condition, inhibition of angiogenesis, treatment of an angiogenic disease or condition, treatment of cancer and precancerous conditions, treatment of a fibrotic disorder, treatment of a viral infection, treatment of an Akt-mediated disease or condition, inhibition of the production, release or both of matrix metalloproteinase-9, and inhibition of Akt activation.

  本发明提供了式I的二酮螺氨酸。本发明还提供了包含该二酮螺氨酸、其药学上可接受的盐或前药作为活性成分的药物组合物。本发明还提供利用式I的二酮螺氨酸的治疗方法，包括抑制增生性疾病或病况、抑制血管生成、治疗血管生成性疾病或病况、治疗癌症和癌前病变、治疗纤维化疾病、治疗病毒感染、治疗Akt介导的疾病或病况、抑制基质金属蛋白酶-9的产生、释放或二者都抑制以及抑制Akt的激活。
• Stereodivergent total synthesis of rocaglaol initiated by synergistic dual-metal-catalyzed asymmetric allylation of benzofuran-3(2H)-one
  作者：Yang Xu、Hongkai Wang、Zhuang Yang、Yuqiao Zhou、Yangbin Liu、Xiaoming Feng

  DOI：10.1016/j.chempr.2022.04.006

  日期：2022.7

  synergistic catalysis of a chiral N,N′-dioxide-Co(or Ni) complex and a phosphoramidite-Ir catalyst. All four possible stereoisomers of the α-allylated product are provided with excellent diastereo- and enantioselectivities by appropriate permutations of the two chiral catalysts. The concise synthesis of the targeted molecule rocaglaol is furnished in a stereodivergent manner, following a uniform synthetic route

  生物活性天然化合物的所有立体异构体的立体发散全合成能够全面评估立体化学结构-活性关系是极具挑战性和价值的。含有紧凑的功能化环戊二烯[ b ]苯并呋喃支架的天然黄酮类化合物显示出广泛的生物活性。在此，我们公开了一种新的 benzofuran-3(2 H )-one 的立体发散烯丙基烷基化，它依赖于手性N的协同催化，N'-二氧化物-Co（或Ni）络合物和亚磷酰胺-Ir催化剂。通过两种手性催化剂的适当排列，α-烯丙基化产物的所有四种可能的立体异构体都具有优异的非对映选择性和对映选择性。目标分子罗卡劳酚的简明合成以立体发散的方式提供，遵循统一的合成路线并使用相同的起始材料组。随后，对八种罗卡劳酚立体异构体的抗癌活性的初步研究揭示了立体化学变化对生物活性的显着影响。