1-甲基-5-(3-硝基苯基)-1H-四唑 | 69746-32-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-甲基-5-(3-硝基苯基)-1H-四唑
• 英文名称: 1-methyl-5-(3-nitrophenyl)-tetrazole
• 英文别名: 1-Methyl-5-m-nitrophenyl-tetrazol；1-methyl-5-(3-nitrophenyl)-1H-Tetrazole；1-methyl-5-(3-nitrophenyl)tetrazole
• CAS: 69746-32-3
• 化学式: C₈H₇N₅O₂
• 分子量: 205.176
• InChiKey: QKAFKWWKUGJFIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  146-148 °C
• 沸点：
  400.9±47.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  89.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-甲基-5-(3-硝基苯基)-1H-四唑 在 palladium on activated charcoal 2,6-二甲基吡啶 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 [3-(1-methyl-1H-tetrazol-5-yl)-phenyl]-carbamic acid phenyl ester
  参考文献：
  名称：

  Discovery of CC Chemokine Receptor-3 (CCR3) Antagonists with Picomolar Potency

  摘要：

  Starting with our previously described(20) class of CC chemokine receptor-3 (CCR3) antagonist, we improved the potency by replacing the phenyl linker of 1 with a cyclohexyl linker and by replacing the 4-benzylpiperidine with a 3-benzylpiperidine. The resulting compound, 32, is a potent and selective antagonist of CCR3. SAR studies showed that the 3-acetylphenyl urea of 32 could be replaced with heterocyclic ureas or heterocyclic-substituted phenyl ureas and still maintain the potency (inhibition of eotaxin-induced chemotaxis) of this class of compounds in the low-picomolar range (IC50 = 10-60 pM), representing some of the most potent CCR3 antagonists reported to date. The potency of 32 for mouse CCR3 (chemotaxis IC50 = 41 nM) and its oral bioavailability in mice (20% F) were adequate to assess the efficacy in animal models of allergic airway inflammation. Oral administration of 32 reduced eosinophil recruitment into the lungs in a dose-dependent manner in these animal models. On the basis of its overall potency, selectivity, efficacy, and safety profile, the benzenesulfonate salt of 32, designated DPC168, entered phase 1 clinical trials.

  DOI：

  10.1021/jm049530m
• 作为产物：
  描述：

  N-甲基-3-硝基苯甲酰胺 在 sodium azide 、 三氟甲磺酸酐 作用下， 以 乙腈 为溶剂， 反应 3.5h， 以72%的产率得到1-甲基-5-(3-硝基苯基)-1H-四唑
  参考文献：
  名称：

  N-substituted heterocyclic amines as modulators of chemokine receptor activity

  摘要：

  本申请描述了化学式(I)的趋化因子受体调节剂或其药用盐形式，可用于预防哮喘和其他过敏性疾病。

  公开号：

  US20040067935A1

文献信息

• N-ureidoheterocycloalkyl-piperidines as modulators of chemokine receptor activity
  申请人：——

  公开号：US20030032654A1

  公开（公告）日：2003-02-13

  The present application describes modulators of CCR3 of formula (I): 1 or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.

  本申请描述了CCR3的调节剂，其化学公式为(I)： 1 或其药用可接受的盐形式，用于预防哮喘和其他过敏性疾患。
• Benzodiazepine derivatives, compositions containing them and their use in therapy
  申请人：MERCK SHARP & DOHME LTD.

  公开号：EP0514133A1

  公开（公告）日：1992-11-19

  Compounds of formula (I), and salts and prodrugs thereof wherein:    R¹ represents optionally substituted C₁₋₆alkyl or C₃₋₇cycloalkyl;    R² represents an optionally substituted phenyl or pyridyl group;    R³ represents C₁₋₆ alkyl or halo;    R⁴ represents C₃₋₇ cycloalkyl;    X is 0, 1, 2 or 3; are CCK and/or gastrin antagonists. They and compositions thereof are therefore useful in therapy.

  公式(I)的化合物，以及其盐和前药，其中：R¹代表可选地取代的C₁₋₆烷基或C₃₋₇环烷基；R²代表可选地取代的苯基或吡啶基团；R³代表C₁₋₆烷基或卤素；R⁴代表C₃₇环烷基；X是0、1、2或3；是CCK和/或胃泌素拮抗剂。它们及其组合物因此在治疗中是有用的。
• N-substituted heterocyclic amines as modulators of chemokine receptor activity
  申请人：——

  公开号：US20040067935A1

  公开（公告）日：2004-04-08

  The present application describes modulators of chemokine receptors of formula (I): 1 or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.

  本申请描述了化学式(I)的趋化因子受体调节剂或其药用盐形式，可用于预防哮喘和其他过敏性疾病。
• Benzodiazepine derivatives and their use as antagonists of
  申请人：Merck, Sharp & Dohme, Ltd.

  公开号：US05696110A1

  公开（公告）日：1997-12-09

  ##STR1## Compounds of formula (I), and salts and prodrugs thereof, wherein X is O,S,NR.sup.4 or CH.sub.2 ; R.sup.1 represents H, certain optionally substituted C.sub.1-6 alkyl, or C.sub.3-7 cycloalkyl; R.sup.2 represents phenyl having certain optional substituents; R.sup.3 represents C.sub.1-6 alkyl, halo or NR.sup.6 R.sup.7 ; m is 2,3 or 4; n is 1,2,3,4,5,6 7 or 8 when X is CH.sub.2 or 2,3,4,5,6,7 or 8 when X is O, S or NR.sup.4 ; and x is 0,1,2, or 3; are CCK and/or gastrin antagonists. They and compositions thereof are therefore useful in therapy.

  化学式(I)的化合物，及其盐和前药，其中X是O、S、NR.sup.4或CH.sub.2；R.sup.1代表H、某些可选择取代的C.sub.1-6烷基，或C.sub.3-7环烷基；R.sup.2代表具有某些可选取代基团的苯基；R.sup.3代表C.sub.1-6烷基、卤素或NR.sup.6 R.sup.7；m为2、3或4；当X为CH.sub.2时，n为1、2、3、4、5、6、7或8，当X为O、S或NR.sup.4时，n为2、3、4、5、6、7或8；x为0、1、2或3；它们是CCK和/或胃泌素拮抗剂。因此，它们及其组合物在治疗中是有用的。
• A facile and convenient synthesis of substituted tetrazole derivatives from ketones or α,β-unsaturated ketones
  作者：Abdel-Aziz S. El-Ahl、Saad S. Elmorsy、Hanan Soliman、Fathy A. Amer

  DOI：10.1016/0040-4039(95)01513-h

  日期：1995.10

  Triazidochlorosilane (SiCl4 - NaN3 in situ) is a new and efficient reagent for the direct conversion of ketones or α,β-unsaturated ketones to the corresponding tetrazole derivatives in nearly quantitative yield.

  三叠氮氯硅烷（SiCl 4 -NaN 3原位反应）是一种新的有效试剂，可将酮或α，β-不饱和酮直接转化为相应的四唑衍生物，且定量接近收率。