2-(3,3-二苯基丙基)丙二酸 | 101790-37-8

• 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-(3,3-二苯基丙基)丙二酸
• 英文名称: 2-(3,3-diphenylpropyl)malonic acid
• 英文别名: (3,3-diphenyl-propyl)-malonic acid；(3,3-Diphenyl-propyl)-malonsaeure；2-(3,3-Diphenylpropyl)propanedioic acid
• CAS: 101790-37-8
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: DJLQJICSPFHQIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,3-二苯基丙基)丙二酸 在 硫酸 作用下， 以 氯仿 为溶剂， 反应 5.0h， 生成 5,5-diphenyl-valeric acid methyl ester
  参考文献：
  名称：

  New 1,3-dioxolane and 1,3-dioxane derivatives as effective modulators to overcome multidrug resistance

  摘要：

  Multidrug resistance (MDR) to antitumor agents represents a major obstacle to a successful chemotherapy of cancer. Overexpression of P-glycoprotein (p-gp) seems to be the major factor responsible for MDR. A large number of chemically unrelated compounds are known to interact with p-gp resulting in a decreasing resistance. In our efforts related to structure-activity studies of new potential MDR reversal agents we synthesized a series of compounds that differ in the aromatic core structure, the linker, and the basic moiety. For our search of new aromatic core structures we synthesized novel 2,2-diphenyl-1,3-dioxolane, 2,2- diphenyl-1,3-dioxane, and 4,5-diphenyl-1,3-dioxolane derivatives. A range of lipophilic linker structures and protonable basic moieties were synthesized and investigated to optimize the structure of the potential MDR-modulators. The compounds were tested in vitro using human Caco-2 cells. Both the cytotoxicity of the synthons and their ability to resensitize the cells were determined with a MTT assay. The results show that at low concentration various substances reverse tumor cell MDR. Some of the new structures show better effects than established modulators like trifluoperazine. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.024
• 作为产物：
  描述：

  乐卡地平相关化合物1 在 sodium hydride 、 sodium iodide 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 4.67h， 生成 2-(3,3-二苯基丙基)丙二酸
  参考文献：
  名称：

  Potent Heterocyclic Ligands for Human Complement C3a Receptor

  摘要：

  The G-protein coupled receptor (C3aR) for human inflammatory protein complement C3a is an important component of immune, inflammatory, and metabolic diseases. A flexible compound (N2-[(2,2-diphenylethoxy)acetyl]-l-arginine, 4), known as a weak C3aR antagonist (IC50 mu M), was transformed here into potent agonists (EC50 nM) of human macrophages (Ca2+ release in HMDM) by incorporating aromatic heterocycles. Antagonists were also identified. A linear correlation between binding affinity for C3aR and calculated hydrogen-bond interaction energy of the heteroatom indicated that its hydrogen-bonding capacity influenced ligand affinity and function mediated by C3aR. Hydrogen-bond accepting heterocycles (e.g., imidazole) conferred the highest affinity and agonist potency (e.g., 21, EC50 24 nM, Ca2+, HMDM) with comparable efficacy and immunostimulatory activity as that of C3a in activating human macrophages (Ca2+, IL1 beta, TNF alpha, CCL3). These potent and selective modulators of C3aR, inactivated by a C3aR antagonist, are stable C3a surrogates for interrogating roles for C3aR in physiology and disease.

  DOI：

  10.1021/jm500956p

文献信息

• Synthesis and cardiovascular activity of a new series of cyclohexylaralkylamine derivatives related to perhexiline
  作者：Gerard Leclerc、Nicole Decker、Jean Schwartz

  DOI：10.1021/jm00348a019

  日期：1982.6

  A series of 24 cyclohexylaralkylamine derivatives related to perhexiline has been synthesized and screened for cardiovascular activity. All the compounds contained an exocyclic amine which was substituted either by an alkyl, cycloalkyl, or aralkyl group. In the hope of further reducing toxicity, the synthesis of p-tolyl- and p-hydroxyphenyl derivatives 23 and 24 was undertaken. The effect of separating

  已经合成了一系列与哌己啉相关的24种环己基烷基胺衍生物，并筛选了其心血管活性。所有化合物都含有被烷基，环烷基或芳烷基取代的环外胺。为了进一步降低毒性，进行了对甲苯基和对羟基苯基衍生物23和24的合成。已经系统地检查了相对于芳核分离环己胺部分的效果。根据以下标准顺序，进行药理学研究，以寻找活性优于哌克西林的化合物：（1）α-肾上腺素分解活性；（2）增加冠状动脉血流量；（3）钙拮抗作用。几种化合物比哌克西林更有效，毒性更低。
• Histaprodifens:  Synthesis, Pharmacological in Vitro Evaluation, and Molecular Modeling of a New Class of Highly Active and Selective Histamine H₁-Receptor Agonists
  作者：Sigurd Elz、Kai Kramer、Heinz H. Pertz、Heiner Detert、Anton M. ter Laak、Ronald Kühne、Walter Schunack

  DOI：10.1021/jm991056a

  日期：2000.3.1

  A new class of histamine analogues characterized by a 3, 3-diphenylpropyl substituent at the 2-position of the imidazole nucleus has been prepared outgoing from 4,4-diphenylbutyronitrile (4b) via cyclization of the corresponding methyl imidate 5b with 2-oxo-4-phthalimido-1-butyl acetate or 2-oxo-1,4-butandiol in liquid ammonia, followed by standard reactions. The title compounds displayed partial agonism

  通过将相应的亚氨酸甲酯5b与2-氧代-环戊基环合，从4,4-二苯基丁腈（4b）制备了一类新的组胺类似物，其特征是在咪唑核的2位上有一个3，3-二苯丙基取代基。在液氨中的4-邻苯二甲酰亚胺基-1-乙酸丁酯或2-氧代-1,4-丁二醇，然后进行标准反应。标题化合物分别对豚鼠回肠和内皮剥脱的主动脉的收缩性H（1）受体表现出部分激动作用，但10（组胺布洛芬; 2- [2-（3，3-二苯丙基）-1H-咪达唑-4）除外-基]乙胺），在回肠测定中是完全激动剂。虽然10与组胺（1）等价，但是甲基组蛋白（13）和二甲基组蛋白（14）的功能效价比1高出3-5（13）和2-3（14）。化合物10和13-17放松了预收缩的大鼠主动脉环（完整内皮），相对效力为3.3至28倍（与1相比），也表现出部分激动作用。激动剂的作用对选择性H（1）-受体拮抗剂美吡拉敏（pA（2）约9（几内亚猪）和pA（2）约8（大鼠主动脉）的封
• Salmon-Legagneur; Neveu, Bulletin de la Societe Chimique de France, 1956, p. 929,936
  作者：Salmon-Legagneur、Neveu

  DOI：——

  日期：——