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。
• 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。
• [EN] SUBSTITUTED SPIRO AZABICYCLICS AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY<br/>[FR] DERIVES SPIRO AZABICYCLIQUES SUBSTITUES EN TANT QUE MODULATEURS DE L'ACTIVITE DU RECEPTEUR DE LA CHIMIOKINE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2005080376A1

  公开（公告）日：2005-09-01

  The present application describes modulators of CCR3 of formula (Ia) and (Ib): (I) or pharmaceutically acceptable salt forms thereof, wherein Z, R1, R2, R3, R4, R5, R5', R6, a, b, c, d, and u are as defined herein. In addition, methods of treating and preventing inflammatory diseases such as asthma and allergic diseases, as well as autoimmune pathologies such as rheumatoid arthritis and atherosclerosis using said modulators are disclosed.

  本申请描述了公式(Ia)和(Ib)的CCR3调节剂：(I)或其药用可接受的盐形式，其中Z、R1、R2、R3、R4、R5、R5'、R6、a、b、c、d和u的定义如本文所述。此外，还公开了利用这些调节剂治疗和预防哮喘和过敏性疾病等炎症性疾病，以及类风湿关节炎和动脉粥样硬化等自身免疫病理的方法。