1-苯基-3-甲硫基-4-氰基-5-氨基-1H-吡唑 | 59334-11-1

• 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-苯基-3-甲硫基-4-氰基-5-氨基-1H-吡唑
• 英文名称: 5-amino-3-(methylsulfanyl)-1-phenyl-1H-pyrazole-4-carbonitrile
• 英文别名: 5-amino-3-(methylthio)-1-phenyl-1H-pyrazole-4-carbonitrile；5-amino-3-methylthio-1-phenyl-1H-pyrazole-4-carbonitrile；5-amino-4-cyano-3-methylsulfanyl-1-phenyl-1H-pyrazole；5-amino-3-methylthio-1-phenylpyrazole-4-carbonitrile；5-amino-4-cyano-3-(methylthio)-1-phenylpyrazole；5-amino-4-cyano-3-methylthio-1-phenylpyrazole；5-amino-3-methylsulfanyl-1-phenylpyrazole-4-carbonitrile
• CAS: 59334-11-1
• 化学式: C₁₁H₁₀N₄S
• mdl: MFCD00173846
• 分子量: 230.293
• InChiKey: IIOQJYJHSDCILE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  92.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  1-苯基-3-甲硫基-4-氰基-5-氨基-1H-吡唑 在 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 反应 14.0h， 生成 4-chloro-3-methylsulphanyl-1-phenyl-pyrazolo[3,4-d]pyrimidine
  参考文献：
  名称：

  COX-1/COX-2 inhibition assays and histopathological study of the new designed anti-inflammatory agent with a pyrazolopyrimidine core

  摘要：

  Four pyrazolopyrimidine series were prepared with a substitution at position-4 by Schiff base, triazole, oxadiazole and pyrazole moieties (7a-f, 8a,b, 9a-f, 10a,b and 13a,b), respectively. All the synthesized compounds were evaluated in vitro against COX-2 and in vivo against carrageenan-induced rat paw edema as anti-inflammatory agents. Regarding the anti-inflammatory activity (AI) compounds 7c, 7f, 8a, and 9a showed higher activity with respect to celecoxib. Compounds 9a, 7d, and 7f were closely selective to celecoxib. Also, 7c and 7d were safer than indomethacin and similar to celecoxib as resulted from the histopathological study. In addition, the docking study that showed the binding mode of prominent pyrazolopyrimidine compounds inside the COX-2 receptor. Formation of unexpected pyrazole 13a and 13b was briefly discussed using 2D NMR.

  DOI：

  10.1016/j.bioorg.2019.01.031
• 作为产物：
  描述：

  [双(甲硫基)亚甲基]丙烷二腈 在 苯肼 作用下， 以 乙醇 为溶剂， 以91%的产率得到1-苯基-3-甲硫基-4-氰基-5-氨基-1H-吡唑
  参考文献：
  名称：

  Method of quantitative determination of peroxides, a peroxidation-active substance or a pyrazolopyridopyridazine derivative

  摘要：

  公开号：

  EP0745684B1

文献信息

• Studies on Phosphoroheterocycle Chemistry II: A Simple and New Route to 1, 3, 2-Diazaphospholidine-4-thione 2-sulfide Derivatives
  作者：ShengLou Deng、DongZhi Liu

  DOI：10.1055/s-2001-18708

  日期：——

  A simple and new method for the synthesis of phosphoroheterocycles 1,3,2-diazaphospholidine-4-thione 2-sulfide derivatives by treatment of Lawesson’s reagent (LR) with a variety of α-aminonitriles has been developed. The same methodology was also used in the preparation of fused phosphoroheterocycle 6 from 5-amino-4-cyano-3-methylthia-1-phenylpyrazole. The possible mechanism of the reaction involving addition of P-SH to the nitrile and subsequent rearrangement is proposed.

  开发了一种简单新颖的方法，通过Lawesson试剂（LR）与多种α-氨基腈反应合成磷杂环1,3,2-二氮磷杂环-4-硫酮-2-硫化物衍生物。同样的方法也被用于从5-氨基-4-氰基-3-甲基硫-1-苯基吡唑制备融合磷杂环6。提出了可能的反应机理，涉及P-SH对氰基的加成以及随后的重排。
• Facile Method for the Synthesis of Pyrazolo[3,4-b]-pyrido[4,3-d]-pyrimidine-4-ones via a Tandem Aza-Wittig Reaction
  作者：Tao Wang、Cai Hua Zheng、Shu Liu、Hong Wu He

  DOI：10.1080/00397910902730895

  日期：2009.9.8

  Abstract Fifteen novel pyrazolo[3,4-b]-pyrido[4,3-d]-pyrimidine-4-ones (7a–o) were designed and have been successfully synthesized via tandem aza-Wittig and annulation reactions of the corresponding iminophosphorances 5, phenylisocyanate, and substituted phenols in 60–77% isolated yields. Their structures were clearly verified by infrared (IR), 1H NMR, electron impact–mass spectrometry (EI-MS), and

  摘要 设计了 ​​15 种新型吡唑并[3,4-b]-吡啶并[4,3-d]-嘧啶-4-酮（7a-o），并通过串联氮杂-Wittig 和相应亚氨基磷的环化反应成功合成5、异氰酸苯酯和取代酚的分离产率为 60-77%。它们的结构通过红外 (IR)、1H NMR、电子冲击质谱 (EI-MS) 和元素分析得到了明确验证。初步生物测定结果表明，一些化合物在 100 mg/L 和 10 mg/L 的剂量下对欧洲油菜（油菜）和稗子（稗草）的根具有抑制活性。
• Facile Synthesis of Pyrazolo[3,4‐<i>d</i>]pyrimidines and Pyrimido[4,5‐<i>d</i>]pyrimidin‐4‐one Derivatives
  作者：Sanjay Babu Katiyar、Arun Kumar、Prem M. S. Chauhan

  DOI：10.1080/00397910600773726

  日期：2006.10

  (EGFR), antiproliferative, dihydrofolate reductase (DHFR), antimicrobial, antifungal, and lipid peroxidation. Because of this wide range of activities, we have synthesized pyrazolo[3,4‐d]pyrimidines and pyrimido[4,5‐d]pyrimidin‐4‐one derivatives.

  摘要 吡唑并嘧啶和嘧啶并嘧啶衍生物已显示出广泛的生物活性，例如作为 A1 腺苷受体、激酶插入域受体 (KDR)、劳斯肉瘤癌基因 (Src)、表皮生长因子受体 (EGFR)、抗增殖剂、二氢叶酸还原酶 (DHFR)。 )、抗微生物、抗真菌和脂质过氧化。由于这种广泛的活性，我们合成了吡唑并[3,4-d]嘧啶和嘧啶并[4,5-d]嘧啶-4-one衍生物。
• Synthesis and chemiluminescence of 1,3-disubstituted pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyridazine-5,8(6h,7h)-diones and related compounds
  作者：Yoshinori Tominaga、Noriko Yoshioka、Seigo Kataoka、Norihito Aoyama、Toshiyuki Masunari、Akira Miike

  DOI：10.1016/0040-4039(95)01862-c

  日期：1995.11

  [4′,3′:5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-diones (7a-s) in good yields. These tricyclic pyridazine derivatives were evaluated for chemiluminescence. Some were found to be more efficient than luminol in light production. 4-Amino-3-methylsufonyl-1-phenyl-1H-pyrazolo [4′,3′:5,6]pyndo[2,3-d]pyridazine-5,8(6H,7H)-dione(7r) showed the greatest chemiluminescence intensity derivatives in the presence of H2O2

  1,3-二取代的5-氨基吡唑-4-腈衍生物（3a-o）与乙炔二羧酸二甲酯在碳酸钾存在下于二甲亚砜中的反应，得到相应的二甲基1,3-二取代的吡唑并[3,4-b]吡啶-5,6-二羧酸盐（4a-o）与过量的水合肼在乙醇中回流反应，然后在250-300°C加热，得到1,3-二取代的4-氨基-1H-吡唑醇[4' ，3'：5,6] pyrido [2,3-d] pyridazine-5,8（6H，7H）-diones（7a-s）的产率很高。评价这些三环哒嗪衍生物的化学发光。发现一些在发光方面比鲁米诺更有效。4-Amino-3-methylsufonyl-1-phenyl-1H-pyrazolo [4'，3'：5,6] pyndo [2,3-d]哒嗪-5,8（6H，7H）-dione（7r）在过氧化物酶H 2 O 2存在下，在磷酸盐缓冲液pH 8.0中显示出最大的化学发光强度衍生物
• Synthesis of pyrazolo[3,4-<i>d</i>]pyrimidine derivatives using ketene dithioacetals
  作者：Yoshinori Tominaga、Yasumasa Honkawa、Mayumi Hara、Akira Hosomi

  DOI：10.1002/jhet.5570270355

  日期：1990.3

  reaction of ketene dithioacetals 1a,b [1a: bis(methylthiomethylenemalononitrile; 1b: bis(methylthio)methylenecyanoacetamide] with hydrazines (hydrazine hydrate, phenylhydrazine, p-chlorophenylhydrazine, p-nitrophenylhydrazine), with formamide or carbon disulfide proceeded to give the corresponding 4-amino- or 4-hydroxy-3-methylthiopyrazolo[3,4-d]pyrimidines 6a-h in good yields. 3-Aminopyrazolo[3,4-d]pyrimidine

  的5-氨基-3- methylthiopyrazole -4-腈或4-甲酰胺环化3A-J ，这是由乙烯酮二硫反应制备1A，B [1A：双（methylthiomethylenemalononitrile; 1B：二（甲硫基）methylenecyanoacetamide]与肼（水合肼，苯肼，p -chlorophenylhydrazine，p -nitrophenylhydrazine）与甲酰胺或二硫化碳进行，得到相应的4-氨基-或4-羟基-3- methylthiopyrazolo [3,4 d ]嘧啶6A-H在3-氨基吡唑并[3,4- d ]嘧啶衍生物6i-1 通过应用3，5-二氨基吡唑与甲酰胺的环化反应也获得了它们。