2-[[(2’-氰基联苯-4-基)甲基]氨基]-3-硝基苯甲酸乙酯 | 136285-67-1

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 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-[[(2’-氰基联苯-4-基)甲基]氨基]-3-硝基苯甲酸乙酯
• 中文别名: 2-[[(2'-氰基联苯-4-基)甲基]氨基]-3-硝基苯甲酸乙酯；2-[[(2'-氰基联苯-4-基)甲基]氨基]-3-硝基苯甲酸乙酯,坎地沙坦酯/阿奇沙坦中间体；坎地沙坦酯中间体C4；坎地沙坦中间体乙酯C4；2-[[(2-氰基联苯-4-基)甲基]氨基]-3-硝基苯甲酸乙酯
• 英文名称: ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]amino-3-nitrobenzoate
• 英文别名: ethyl 2-[[(2'-cyanobiphenyl-4-yl)methyl]amino]nitrobenzoate；Ethyl-2-[[(2'-cyanobiphenyl-4-YL)methyl]amino]-3-nitrobenzoate；ethyl 2-[[4-(2-cyanophenyl)phenyl]methylamino]-3-nitrobenzoate
• CAS: 136285-67-1
• 化学式: C₂₃H₁₉N₃O₄
• mdl: MFCD09030634
• 分子量: 401.422
• InChiKey: CHPMKOFPDCKNBG-UHFFFAOYSA-N

物化性质

• 熔点：
  >209°C (dec.)
• 沸点：
  602.9±55.0 °C(Predicted)
• 密度：
  1.31
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

制备方法

新型非肽类长效ATII受体拮抗剂，高效抗高血压原料药坎地沙坦酯中间体。

用途简介

（暂时没有内容）

反应信息

• 作为反应物：
  描述：

  2-[[(2’-氰基联苯-4-基)甲基]氨基]-3-硝基苯甲酸乙酯 在 tin(II) chloride dihdyrate 、 溶剂黄146 作用下， 反应 3.0h， 生成 2-乙氧基-1-[[(2'-腈基连苯-4-取代)甲基]苯并咪唑]-7-羧酸乙酯
  参考文献：
  名称：

  Synthesis, characterization of benzimidazole carboxamide derivatives as potent anaplastic lymphoma kinase inhibitor and antioxidant activity

  摘要：

  Novel benzimidazole carboxamide derivatives have been synthesized and characterized by FTIR, NMR, and mass spectral analysis. The synthesized compounds 7a, 7d, and 7f showed excellent scavenging capacity against DPPH radical and the results are comparable with ascorbic acid. In-silico molecular docking studies exhibited compounds 7a, 7d, and 7f had a good affinity towards the active pocket and the results indicated the ability of potent and selective inhibition of anaplastic lymphoma kinase (ALK) receptor. The theoretical investigation of MEPs, HOMO, LUMO, and the energy gap of HOMO-LUMO were calculated by B3LYP/6-31G method and reactivity descriptors were also computed.[GRAPHICS]

  DOI：

  10.1080/00397911.2018.1554144
• 作为产物：
  描述：

  2-氨基-3-硝基苯甲酸乙酯 在 sodium hydride 作用下， 反应 1.0h， 生成 2-[[(2’-氰基联苯-4-基)甲基]氨基]-3-硝基苯甲酸乙酯
  参考文献：
  名称：

  Synthesis, characterization of benzimidazole carboxamide derivatives as potent anaplastic lymphoma kinase inhibitor and antioxidant activity

  摘要：

  Novel benzimidazole carboxamide derivatives have been synthesized and characterized by FTIR, NMR, and mass spectral analysis. The synthesized compounds 7a, 7d, and 7f showed excellent scavenging capacity against DPPH radical and the results are comparable with ascorbic acid. In-silico molecular docking studies exhibited compounds 7a, 7d, and 7f had a good affinity towards the active pocket and the results indicated the ability of potent and selective inhibition of anaplastic lymphoma kinase (ALK) receptor. The theoretical investigation of MEPs, HOMO, LUMO, and the energy gap of HOMO-LUMO were calculated by B3LYP/6-31G method and reactivity descriptors were also computed.[GRAPHICS]

  DOI：

  10.1080/00397911.2018.1554144

文献信息

• Benzimidazole derivatives and their use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05128356A1

  公开（公告）日：1992-07-07

  Novel imidazole derivatives of the formula (I): ##STR1## wherein R.sup.1 is an optionally substituted alkyl group, R.sup.2 and R.sup.3 are independently a group capable of forming an anion or a group which can be changed thereinto, ring A is a benzene ring optionally having, besides the group shown by R.sup.2, further substituents, and X shows linkage of phenylene group and phenyl group directly or through a spacer whose atomic length is not more than 2 and a salt thereof, show antagonistic actions to angiotensin II, thus being useful as therapeutics for cardiovascular diseases.

  新型咪唑衍生物的公式（I）如下：##STR1##，其中R.sup.1是一个可选地取代的烷基团，R.sup.2和R.sup.3独立地是能够形成阴离子或可以转变为阴离子的基团，环A是一个苯环，除了R.sup.2所示的基团外，还可以有其他取代基，而X表示苯基团和苯基团直接连接或通过一个原子长度不超过2的间隔物连接，以及它们的盐，对血管紧张素II显示出拮抗作用，因此作为治疗心血管疾病的药物是有用的。
• 1-(cyclohexyloxycarbonyloxy)ethyl
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05196444A1

  公开（公告）日：1993-03-23

  1-(Cyclohexyloxycarbonyloxy)ethyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-car boxylate or a pharmaceutically acceptable salt thereof has potent angiotensin II antihypertensive activity, thus being useful as therapeutic agents for treating circulatory system diseases such as hypertensive diseases, heart diseases (e.g. hypercardia, heart failure, cardiac infarction, etc.), strokes, cerebral apoplexy, nephritis, etc.

  1-(环己氧羰氧基)乙基2-乙氧基-1-[[2'-(1H-四唑-5-基)联苯-4-基]甲基]苯并咪唑-7-羧酸酯或其药学上可接受的盐具有强效的血管紧张素II抗高血压活性，因此可用作治疗循环系统疾病，如高血压、心脏疾病（如心动过速、心力衰竭、心肌梗死等）、中风、脑卒中、肾炎等的治疗药物。
• 苯并咪唑衍生物及其制备和用途
  申请人：武田药品工业株式会社

  公开号：CN1055927A

  公开（公告）日：1991-11-06

  公开了一种下式(I)的苯并咪唑衍生物及其药用盐以及它们的制备方法，其中各基团如说明书所示。所述衍生物具有强有力的血管紧张素II拮抗活性和抗高血压活性，从而可用作治疗高血压、心脏病、中风、大脑卒中、肾炎等循环系统的疾病用的治疗剂。
• Benzimidazole derivatives, their production and use
  申请人：Naka Takehiko

  公开号：US20070259932A1

  公开（公告）日：2007-11-08

  Benzimidazole derivatives of the formula (I): wherein the ring A is a benzene ring which may optionally contain substitution in addition to the R′ group; R 1 is hydrogen or an optionally substituted hydrocarbon residue; R 2 is a group capable of forming an anion or a group convertible thereinto; X is a direct bond or a spacer having an atomic length of two or less between the phenylene group and the phenyl group; R′ is carboxyl, an ester thereof, an amide thereof or a group capable of forming an anion or convertible to an anion; Y is —O—, —S(O) m — or —N(R 4 )— wherein m is an integer of 0, 1 or 2 and R 4 is hydrogen or an optionally substituted alkyl group; and n is an integer of 1 or 2; and the pharmaceutically acceptable salts thereof, have potent angiotensin II antagonistic activity and antihypertensive activity, thus being useful as therapeutic agents for treating circulatory system diseases such as hypertensive diseases, heart diseases (e.g. hypercardia, heart failure, cardiac infarction, etc.), strokes, cerebral apoplexy, nephritis, etc.

  公式（I）中的苯并咪唑衍生物： 其中环A是苯环，除了R′基之外，还可以选择性地含有取代基；R1是氢或可选择性取代的碳氢基；R2是能够形成负离子或可转化为负离子的基团；X是直接键或具有原子长度为两个或更少的间隔物，在苯基团和苯基团之间；R′是羧基，其酯，其酰胺或能够形成负离子或可转化为负离子的基团；Y是-O-，-S（O）m-或-N（R4）-，其中m是0、1或2的整数，R4是氢或可选择性取代的烷基；n是1或2的整数；以及其药物学上可接受的盐，具有强大的血管紧张素II拮抗活性和降压活性，因此可用作治疗循环系统疾病，如高血压疾病、心脏疾病（例如心脏肥大、心力衰竭、心肌梗塞等）、中风、脑卒中、肾炎等的治疗剂。
• Pivaloyloxymethyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl) biphenyl-4-yl]
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05328919A1

  公开（公告）日：1994-07-12

  Pivaloyloxymethyl2-ethoxy-1-[['-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benz imidazole-7-carboxylate or a pharmaceutically acceptable salt thereof has potent angiotensin II antagonistic activity and antihypertensive activity, thus being a useful therapeutic agent for treating circulatory system diseases such as hypertensive diseases, heart diseases (e.g. hypercardia, heart failure, cardiac infarction, etc.), strokes, cerebral apoplexy or nephritis.

  Pivaloyloxymethyl2-ethoxy-1-[['-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylate或其药学上可接受的盐具有强大的血管紧张素II拮抗活性和降压活性，因此是治疗循环系统疾病（如高血压病，心脏病（例如心肌病，心力衰竭，心肌梗死等），中风，脑卒中或肾炎）的有用治疗剂。