2'-aminomethylbiphenyl-2-carboxylic acid | 31638-34-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2'-aminomethylbiphenyl-2-carboxylic acid
• 英文别名: aminomethyl-(1,1'-biphenyl)-2-carboxylic acid；2'-(aminomethyl)-biphenyl-2-carboxylic acid；2-[2-(aminomethyl)phenyl]benzoic acid
• CAS: 31638-34-3
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: IPUFFJSTKHPCBZ-UHFFFAOYSA-N

物化性质

• 沸点：
  415.6±33.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 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：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2'-aminomethylbiphenyl-2-carboxylic acid 在 sodium hydroxide 、 1-羟基苯并三唑 、 三氟乙酸 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 2'-Aminomethylbiphenyl-2-carboxylic Acid Isopentylamide
  参考文献：
  名称：

  Identification, Synthesis, and Activity of Novel Blockers of the Voltage-Gated Potassium Channel Kv1.5

  摘要：

  The voltage-gated potassium channel Kv1.5 is regarded as a promising target for the development of new atrial selective drugs with fewer side effects. In the present study the discovery of ortho,ortho-disubstituted bisaryl compounds as blockers of the Kv1.5 channel is presented. Several compounds of this new class were synthesized and screened for their ability to block Kv1.5 channels expressed in Xenopus oocytes. The observed structure-activity relationship (SAR) is described by a pharmacophore model that consists of three hydrophobic centers in a triangular arrangement. The hydrophobic centers are matched by a phenyl or pyridyl ring of the bisaryl core and both ends of the side chains. The most potent compounds (e.g., 17c and 17o) inhibited the Kv1.5 channel with sub-micromolar half-blocking concentrations and displayed 3-fold selectivity over Kv1.3 and no significant effect on the HERG channel and sodium currents. In addition, compounds 17c and 17m have already shown antiarrhythmic effects in a pig model.

  DOI：

  10.1021/jm0210461
• 作为产物：
  描述：

  10-nitrosophenanthren-9-ol 在 镍 氢气 作用下， 生成 2'-aminomethylbiphenyl-2-carboxylic acid
  参考文献：
  名称：

  Mesnard; Dupin; Brasington, European Journal of Medicinal Chemistry, 1975, vol. 10, # 3, p. 315 - 322

  摘要：

  DOI：

文献信息

• PEPTIDES AND PEPTIDOMIMETIC COMPOUNDS, THE MANUFACTURING THEREOF AS WELL AS THEIR USE FOR PREPARING A THERAPEUTICALLY AND/OR PREVENTIVELY ACTIVE PHARMACEUTICAL COMPOSITION
  申请人：PETZELBAUER Peter

  公开号：US20100081787A1

  公开（公告）日：2010-04-01

  Peptides, peptidomimetics and derivatives thereof of the general formula I: H 2 N-GHRPX 1 - β -X 4 X 5 X 6 X 7 X 8 X 9 X 10 -X 11 (I), in which X 1 -X 10 denote one of the 20 genetically coded amino acids, wherein X 8 , X 9 and X 10 may also denote a single chemical bond; X 11 denotes OR 1 in which R 1 equals hydrogen or (C 1 -C 10 ) alkyl NR 2 R 3 with R 2 and R 3 are equal or different and denote hydrogen, (C 1 -C 10 ) alkyl, or a residue —W-PEG 5-60K , in which the PEG residue is attached via a suitable spacer W to the N-atom, or a residue NH—Y-Z-PEG 5-60K , in which Y denotes a chemical bond or a genetically coded amino acids from the group S, C, K or R and Z denotes a spacer, via which a polyethylene glycol (PEG)-residue can be attached, and their physiologically acceptable salts, and β denotes an amino acid, or a peptidomimetic element, which induces a bend or turn in the peptide backbone.

  通用公式I：H2N-GHRPX1-β-X4X5X6X7X8X9X10-X11(I)中的肽、肽类似物和衍生物，其中X1-X10表示20种遗传编码的氨基酸之一，其中X8、X9和X10也可以表示单一化学键；X11表示OR1，其中R1等于氢或(C1-C10)烷基NR2R3，其中R2和R3相同或不同，表示氢、(C1-C10)烷基，或者残基—W-PEG5-60K，其中PEG残基通过适当的间隔物W连接到N-原子，或者残基NH—Y-Z-PEG5-60K，其中Y表示化学键或来自S、C、K或R组的遗传编码氨基酸，Z表示间隔物，通过该间隔物可以连接聚乙二醇（PEG）残基，并且它们的生理上可接受的盐，β表示氨基酸或诱导肽骨架中弯曲或转弯的肽类或肽类似元素。
• Antiparallel ?-Sheet Conformation in Cyclopeptides Containing a Pseudo-amino Acid with a biphenyl moiety
  作者：Volker Brandmeier、Wolfgang H. B. Sauer、Martin Feigel

  DOI：10.1002/hlca.19940770110

  日期：1994.2.9

  The biphenyl-containing pseudo-amino acids 2′-(aminomethyl)biphenyl-2-carboxylic acid (Abc; 1) and 2′-(aminomethyl)biphenyl-2-acetic acid (Aba; 2) are used as rigid spacers in the backbone of the cyclic peptides cyclo (-Abc-Ala-Phe-Gly-)2 (5), cyclo(-Abc-Ala-Val-Gly-)2 (6), cyclo(-Aba-Gly-Phe-Ala-)2 (7), and cyclo(-Aba-Ala-Phe-Gly-)2(8). Three different interconverting diastereoisomers are found in

  含联苯的假氨基酸2'-（氨基甲基）联苯-2-羧酸（Abc; 1）和2'-（氨基甲基）联苯-2-乙酸（Aba; 2）被用作硬性间隔基环状肽的骨架环（-Abc-Ala-Phe-Gly-）2（5），环（-Abc-Ala-Val-Gly-）2（6），环（-Aba-Gly-Phe-Ala- ）2（7）和环（-Aba-Ala-Phe-Gly-）2（8）。由于联苯单元的阻转异构性，在每种环肽的溶液中发现了三种不同的互变非对映异构体。NMR技术和分子动力学计算可以得出结论，（D 6）DMSO中5（和6）的主要非对映异构体采用β-折叠构象。本发明提出，伪氨基酸1的（- [R）-chirality形式，具有连接的L-氨基酸，相当于β转角的H结合图案（参见d在图4和˚F）。
• [DE] 2'-SUBSTITUIERTE 1,1'-BIPHENYL-2-CARBONAMIDE, VERFAHREN ZU IHRER HERSTELLUNG, IHRE VERWENDUNG ALS MEDIKAMENT SOWIE SIE ENTHALTENDE PHARMAZEUTISCHE ZUBEREITUNGEN<br/>[EN] 2'-SUBSTITUTED 1,1'-BIPHENYL-2-CARBONAMIDES, METHOD FOR THE PRODUCTION THEREOF, USE THEREOF AS A MEDICAMENT AND PHARMACEUTICAL PREPARATIONS CONTAINING SAID COMPOUNDS<br/>[FR] 1,1'-BIPHENYL-2-CARBONAMIDES 2'-SUBSTITUES, PROCEDE DE FABRICATION, UTILISATION EN TANT QUE MEDICAMENT, AINSI QUE PREPARATIONS PHARMACEUTIQUES CONTENANT CES COMPOSES
  申请人：AVENTIS PHARMA GMBH

  公开号：WO2001025189A1

  公开（公告）日：2001-04-12

  Verbindungen der Formel (I), worin R(1), R(2), R(3), R(4), R(5), R(6), R(7), R(8), R(30) und R(31) die in den Ansprüchen angegebenen Bedeutungen haben, sind ganz besonders geeignet als neuartige antiarrhythmische Wirkstoffe, insbesondere zur Behandlung und Prophylaxe von Vorhof-Arrhythmien, z.B. Vorhofflimmern (atriale Fibrillation, AF) oder Vorhoff-Flattern (atriales Flattern).

  公式（I）中的R（1），R（2），R（3），R（4），R（5），R（6），R（7），R（8），R（30）和R（31）具有所述要求中给出的含义，特别适用于作为新型抗心律失常药物，特别是用于治疗和预防心房心律失常，例如心房颤动（房颤）或心房扑动（房扑）。
• 2'-substituted 1,1'-biphenyl-2-carboxamides, process for their preparation, their use as medicaments, and pharmaceutical preparations comprising them
  申请人：Aventis Pharma Deutschland GmbH

  公开号：US20030171351A1

  公开（公告）日：2003-09-11

  Compounds of the formula I, 1 in which R(1), R(2), R(3), R(4), R(5), R(6), R(7), R(8), R(30) and R(31) have the meanings indicated in the claims, are very particularly suitable as novel and antiarrythmic active compounds, in particular for the treatment and prophylaxis of atrial arrythmias, e.g. atrial fibrillation (AF), or atrial flutter.

  化学式为I,1的化合物，其中R(1), R(2), R(3), R(4), R(5), R(6), R(7), R(8), R(30)和R(31)的含义如权利要求中所示，非常适用作为新型和抗心律失常活性化合物，特别是用于治疗和预防心房心律失常，例如心房颤动(AF)或心房扑动。
• 2'-Substituted 1,1'-biphenyl-2-carboxamides, processes for their preparation, their use as medicaments, and pharmaceutical preparations comprising them
  申请人：Aventis Pharma Deutschland GmbH

  公开号：US20040102513A1

  公开（公告）日：2004-05-27

  Compounds of the formula I, 1 in which R(1), R(2), R(3), R(4), R(5), R(6), R(7), R(8), R(30) and R(31) have the meanings indicated in the claims, are very particularly suitable as novel and antiarrythmic active compounds, in particular for the treatment and prophylaxis of atrial arrythmias, e.g. atrial fibrillation (AF), or atrial flutter.

  公式为I,1的化合物，其中R(1)、R(2)、R(3)、R(4)、R(5)、R(6)、R(7)、R(8)、R(30)和R(31)的含义如权利要求所示，非常适用于作为新型和抗心律失常活性化合物，特别适用于治疗和预防心房心律失常，例如心房颤动（AF）或心房扑动。