1-(2,4-dichlorophenyl)-1H-pyrrole | 383137-35-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(2,4-dichlorophenyl)-1H-pyrrole
• 英文别名: 1-(2,4-Dichlorophenyl)pyrrole
• CAS: 383137-35-7
• 化学式: C₁₀H₇Cl₂N
• mdl: MFCD02665218
• 分子量: 212.078
• InChiKey: OEDDJPYZWSNWGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(2,4-dichlorophenyl)-1H-pyrrole 在 aluminum (III) chloride 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 33.5h， 生成 1-[[1-(2,4-dichlorophenyl)-1H-pyrrol-2-yl](2,4-dichlorophenyl)methyl]-1H-imidazole
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of New 1-(Aryl-1H-pyrrolyl)(phenyl)methyl-1H-imidazole Derivatives as Antiprotozoal Agents

  摘要：

  We have designed and synthesized a series of new imidazole-based compounds structurally related to an antiprotozoal agent with nanomolar activity which we identified recently. The new analogues possess micromolar activities against Trypanosoma brucei rhodesiense and Leishmania donovani and nanomolar potency against Plasmodium falciparum. Most of the analogues displayed IC50 within the low nanomolar range against Trypanosoma cruzi, with very high selectivity toward the parasite. Discussion of structure activity relationships and in vitro biological data for the new compounds are provided against a number of different protozoa. The mechanism of action for the most potent derivatives (Si, 6a-c, and 8b) was assessed by a target-based assay using recombinant T. cruzi GYPS1. Bioavailability and efficacy of selected hits were assessed in a T. cruzi mouse model, where 6a and 6b reduced parasitemia in animals >99% following intraperitoneal administration of 25 mg/kg/day dose for 4 consecutive days.

  DOI：

  10.1021/acs.jmedchem.8b01464
• 作为产物：
  描述：

  2,5-二甲氧基四氢呋喃 、 2,4-二氯苯胺 在 iron(III) chloride hexahydrate 作用下， 以 水 为溶剂， 以90%的产率得到1-(2,4-dichlorophenyl)-1H-pyrrole
  参考文献：
  名称：

  Iron-Catalyzed Inexpensive and Practical Synthesis of N-Substituted Pyrroles in Water

  摘要：

  一种操作简便、实用且经济的实验方案已被开发，用于在水相中以铁(III)氯化物为催化剂进行Paal-Knorr吡咯合成，产率良好至优异。在非常温和的反应条件下，多个N-取代吡咯可以方便地通过2,5-二甲氧基四氢呋喃与芳基/烷基、磺酰基和酰基胺的反应来制备。

  DOI：

  10.1055/s-0029-1217799

文献信息

• Salts of bicyclic, N-acylated imidazo-3-amines and imidazo-5-amines
  申请人：GRUENENTHAL GmbH.

  公开号：US20030119842A1

  公开（公告）日：2003-06-26

  Salts of a bicyclic, N-acylated imidazo-3-amine or an imidazo-5-amine of the formula: 1 addition products thereof with acids, and methods for preparing the salts and addition products. Also disclosed are pharmaceutical compositions comprising the same and methods using the pharmaceutical compositions for the treatment or prophylaxis of pain, drug or alcohol abuse, diarrhoea, gastritis, ulcers, urinary incontinence, depression, narcolepsy, overweight, asthma, glaucoma, tinnitus, itching, hyperkinetic syndrome, epilepsy, or schizophrenia, for inducing anesthesia, and for anxiolysis.

  一种具有以下结构的双环N-酰化咪唑-3-胺或咪唑-5-胺的盐：1以及它们与酸的加合物，以及制备这些盐和加合物的方法。还披露了包含这些物质的药物组合物以及使用这些药物组合物治疗或预防疼痛、药物或酒精滥用、腹泻、胃炎、溃疡、尿失禁、抑郁症、嗜睡症、超重、哮喘、青光眼、耳鸣、瘙痒、多动症、癫痫或精神分裂症，用于诱导麻醉和镇静作用的方法。
• SnCl2 Catalyzed Direct Synthesis of Pyrroles under Aqueous Conditions
  作者：D. Tejeswararao、B. Srikanth

  DOI：10.14233/ajchem.2020.22454

  日期：2020.3.10

  Synthetic substituted pyrroles are related with interesting biological activities, yet they remain inadequately explored within drug discovery. Late years have seen a growing interest in synthetic approaches that can provide access to structurally novel pyrroles so that the biological usefulness of this compound class can be more fully investigated. Herein, an efficient and versatile practical protocol for the pyrroles using stannous(II) chloride dihydrate as catalyst is described under aqueous conditions at 55 ºC in high yields. Also, this method is applicable for the preparation of diversity and oriented pyrrole derivatives.

  合成取代吡咯与有趣的生物活性有关，但在药物发现领域仍未得到充分探索。近年来，人们对能够提供结构新颖的吡咯的合成方法越来越感兴趣，以便更全面地研究这一化合物类的生物用途。在这里，描述了一种高效且多功能的吡咯实用方案，使用二水合氯化亚锡(II)作为催化剂，在55摄氏度的水性条件下，产率高。此外，这种方法适用于制备多样性和定向的吡咯衍生物。
• Bicyclic imidazo-5-yl-amine derivatives
  申请人：——

  公开号：US20020183320A1

  公开（公告）日：2002-12-05

  A novel bicyclic imidazo-5-yl-amine derivative of Formula I, 1 wherein X denotes CR 5 , N or S, and Y in the case where X denotes S, denotes CR 6 or N and in all other cases denotes N, and methods for preparation thereof are disclosed. Also disclosed are methods for treating pain using the compound of Formula I, and pharmaceutical compositions comprising the compound of Formula I.

  公开了一种新型的Formula I的双环咪唑-5-基胺衍生物，其中X表示CR5、N或S，当X表示S时，Y表示CR6或N，在所有其他情况下表示N，并公开了其制备方法。还公开了使用Formula I化合物治疗疼痛的方法，以及包含Formula I化合物的药物组合物。
• Bose, D. Subhas; Srikanth, Bingi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016, vol. 55B, # 9, p. 1112 - 1116
  作者：Bose, D. Subhas、Srikanth, Bingi

  DOI：——

  日期：——
• Pyrrole compounds as anti-inflammatory and analgesic agents
  申请人：Merck & Co., Inc.

  公开号：EP0072013B1

  公开（公告）日：1986-04-16