1,2-dichloro-3-ethynylbenzene | 556112-19-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-dichloro-3-ethynylbenzene
• 英文别名: 2,3-dichlorophenylacetylene
• CAS: 556112-19-7
• 化学式: C₈H₄Cl₂
• 分子量: 171.026
• InChiKey: ZJBQVHITAJZERN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,2-dichloro-3-ethynylbenzene 在 copper(l) iodide 、 叠氮基三甲基硅烷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 以71%的产率得到4-(2,3-dichlorophenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Rational Design of 4-Aryl-1,2,3-Triazoles for Indoleamine 2,3-Dioxygenase 1 Inhibition

  摘要：

  Indoleamine 2,3-dioxygenase 1 (IDO1) is an important therapeutic target treatment of diseases such as cancer that involve pathological immune escape. Starting from the scaffold of our previously discovered IDO1 inhibitor 4-phenyl-1,2,3-triazole, we used computational structure-based methods to design more potent ligands. This approach yielded highly efficient low molecular weight inhibitors, the most active being of nanomolar potency both in an enzymatic and in a cellular assay, while showing no cellular toxicity and a high selectivity for IDO1 over tryptophan 2,3-dioxygenase (TDO). A quantitative structure-activity relationship based on the electrostatic ligand-protein interactions in the docked binding modes and on the quantum chemically derived charges of the triazole ring demonstrated a good explanatory power for the observed activities.

  DOI：

  10.1021/jm300260v
• 作为产物：
  描述：

  2,3-二氯碘苯 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 1,2-dichloro-3-ethynylbenzene
  参考文献：
  名称：

  Novel and potent 3-(2,3-dichlorophenyl)-4-(benzyl)-4H-1,2,4-triazole P2X7 antagonists

  摘要：

  Structure-activity relationship (SAR) studies were conducted around early tetrazole-based leads 3 and 4. Replacements for the tetrazole core were investigated and the pendant benzyl substitution was reoptimized with a triazole isostere. Triazole-based P2X(7) antagonists were identified with similar potency to the lead compound 4 but with improved physiochemical properties. Compound 12 was active in a rat model of neuropathic pain. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.075

文献信息

• Novel 3-phenylprop-2-ynylamines as inhibitors of mammalian squalene epoxidaseElectronic supplementary information (ESI) available: Proton NMR spectra for the intermediate piperidines 56–60 and acetylenes 63-81 and 85,86. See http://www.rsc.org/suppdata/ob/b2/b209165h/
  作者：David L. Musso、Morris J. Clarke、James L. Kelley、G. Evan Boswell、Grace Chen

  DOI：10.1039/b209165h

  日期：2003.1.30

  The synthesis of a novel series of 3-phenylprop-2-ynylamines as selective mammalian squalene epoxidase inhibitors is described. Structure–activity relationship studies led to the discovery of compound 19, 1-[3-(3,5-dichlorophenyl)prop-2-ynyl]-3-methylpiperidine hydrochloride with an IC50 of 2.8 ± 0.6 µM against rat liver squalene epoxidase. Against 23 strains of fungal squalene epoxidase compound 19 was found to be inactive.

  报道了一种新型3-苯基丙-2-炔基胺系列化合物的合成，这些化合物是选择性哺乳动物角鲨烯环氧化酶抑制剂。构效关系研究表明，化合物19，即1-[3-(3,5-二氯苯基)丙-2-炔基]-3-甲基哌啶盐酸盐，对大鼠肝脏角鲨烯环氧化酶的IC50值为2.8 ± 0.6 µM。化合物19对23株真菌角鲨烯环氧化酶未显示出活性。
• [EN] NOVEL IMIDAZOLIDINE-2,4-DIONE DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS D'IMIDAZOLIDINE-2,4-DIONE
  申请人：BEAUFOUR IPSEN TIANJIN PHARMACEUTICAL CO LTD

  公开号：WO2015100617A1

  公开（公告）日：2015-07-09

  A subject of the present application is novel imidazolidine-2,4-dione derivatives of formula (I). These products have an anti-proliferative activity. They are particularly useful for treating the pathological states and the diseases linked to an abnormal cell proliferation such as cancers. The invention also relates to the pharmaceutical compositions containing said products and their use for the preparation of a medicament.

  本申请的主题是公式（I）的新型咪唑烷-2,4-二酮衍生物。这些产品具有抗增殖活性，特别适用于治疗与异常细胞增殖相关的病理状态和疾病，如癌症。该发明还涉及含有上述产品的药物组合物以及它们用于制备药物的用途。
• Iron(II)‐Based Metalloradical Activation: Switch from Traditional Click Chemistry to Denitrogenative Annulation
  作者：Satyajit Roy、Hillol Khatua、Sandip Kumar Das、Buddhadeb Chattopadhyay

  DOI：10.1002/anie.201904702

  日期：2019.8.12

  catalytic amount of Fe(TPP)Cl and Zn dust. The reaction precludes the traditional, more favored click reaction between an organic azide and alkynes, and instead proceeds by an unprecedented metalloradical activation. The method is anticipated to advance access to the construction of important basic nitrogen heterocycles, which will in turn enable discoveries of new drug candidates.

  通过催化量的Fe（TPP）Cl和Zn粉尘发现了1,2,3,4-四唑和炔烃的分子间脱氮环化的独特概念。该反应排除了有机叠氮化物和炔烃之间传统的，更受欢迎的点击反应，而是通过空前的金属-金属活化来进行。预计该方法将促进重要的基本氮杂环的构建，而这反过来又可以发现新的候选药物。
• P2X7 receptor antagonists and methods of use
  申请人：Carroll A. William

  公开号：US20070105842A1

  公开（公告）日：2007-05-10

  The invention is directed to compounds that are P2X 7 antagonist and have the formula (I) or (II) or a pharmaceutically acceptable salt, prodrug, salt of a prodrug or a combination thereof, wherein R 1 , R 2 , and R 3 are defined in the specification. The invention is also directed to a method of selectively inhibiting P2X 7 activity comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound of formula (III), (IV) or (V) wherein R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are defined in the specification.

  这项发明涉及具有化学式(I)或(II)的P2X7拮抗剂化合物，或其药学上可接受的盐、前药、前药的盐或二者的组合，其中R1、R2和R3在规范中有定义。该发明还涉及一种选择性抑制P2X7活性的方法，包括向需要此类治疗的患者施用化合物的治疗有效量，其化学式为(III)、(IV)或(V)，其中R6、R7、R8、R9、R10和R11在规范中有定义。
• (Z)-styrylbenzylsulfones and pharmaceutical uses thereof
  申请人：——

  公开号：US20040133030A1

  公开（公告）日：2004-07-08

  Substituted (Z)-styrylbenzyl sulfones of the formulae (I, II, III, IV), pharmaceutically acceptable salts thereof, and compositions thereof are provided as cell antiproliferative agents, including, for example, anticancer agents.

  提供了化学式（I，II，III，IV）的（Z）-苯乙烯基苯基磺酮及其药学上可接受的盐和组合物，作为细胞抗增殖剂，包括例如抗癌剂。