2-(1H-苯并三唑-1-基)乙醇 | 938-56-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 中文名称: 2-(1H-苯并三唑-1-基)乙醇
• 英文名称: 1-(2-hydroxyethyl)-benzotriazole
• 英文别名: 1-<2-Hydroxy-aethyl>-benzotriazol；1H-Benzotriazole-1-ethanol；2-(benzotriazol-1-yl)ethanol
• CAS: 938-56-7
• 化学式: C₈H₉N₃O
• mdl: MFCD00957173
• 分子量: 163.179
• InChiKey: VHEODZYQZLRPTF-UHFFFAOYSA-N

物化性质

• 熔点：
  90-91 °C
• 沸点：
  362.4±25.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(1H-苯并三唑-1-基)乙醇 在 水 、 氢溴酸 、 sodium methylate 作用下， 生成 1,2-bis(benzenetriazol-1-yl)ethane
  参考文献：
  名称：

  Krollpfeiffer et al., Chemische Berichte, 1938, vol. 71, p. 596,602

  摘要：

  DOI：
• 作为产物：
  描述：

  苯并噻唑-1-乙酸 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以59%的产率得到2-(1H-苯并三唑-1-基)乙醇
  参考文献：
  名称：

  Structure−Activity Relationships of 2,N⁶,5‘-Substituted Adenosine Derivatives with Potent Activity at the A_2B Adenosine Receptor

  摘要：

  2, N-6, and 5'-substituted adenosine derivatives were synthesized via alkylation of 2-oxypurine nucleosides leading to 2-arylalkylether derivatives. 2-(3-(Indolyl)ethyloxy)adenosine 17 was examined in both binding and cAMP assays and found to be a potent agonist of the human A(2B)AR. Simplification, altered connectivity, and mimicking of the indole ring of 17 failed to maintain A2BAR potency. Introduction of N-6-ethyl or N-6-guanidino substitution, shown to favor A2BAR potency, failed to enhance potency in the 2-( 3-( indolyl)ethyloxy) adenosine series. Indole 5 ''- or 6 ''-halo substitution was favored at the A(2B)AR, but a 5'-N-ethylcarboxyamide did not further enhance potency. 2-(3 ''-(6 ''-Bromoindolyl)ethyloxy)adenosine 28 displayed an A(2B)AR EC50 value of 128 nM, that is, more potent than the parent 17 (299 nM) and similar to 5'-N-ethylcarboxamidoadenosine (140 nM). Compound 28 was a full agonist at A(2B) and A(2A)ARs and a low efficacy partial agonist at A(1) and A(3)ARs. Thus, we have identified and optimized 2-(2-arylethyl) oxo moieties in AR agonists that enhance A(2B)AR potency and selectivity.

  DOI：

  10.1021/jm061278q
• 作为试剂：
  描述：

  4-cyclopropyl-2-phenylbut-3-yn-2-ol 在 iron(III) chloride 、 2-(1H-苯并三唑-1-基)乙醇 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以85%的产率得到(4-cyclopropylbut-1-en-3-yn-2-yl)benzene
  参考文献：
  名称：

  1,2,3-Triazole: Unique Ligand in Promoting Iron-Catalyzed Propargyl Alcohol Dehydration

  摘要：

  A 1,2,3-traizole-promoted Iron(III)-catalyzed propargyl alcohol dehydration was developed for the synthesis of conjugated enynes. The desired conjugated enynes were prepared in good to excellent yields (up to 95%) with a large substrate scope and excellent stereoselectivity (only Z-isomers).

  DOI：

  10.1021/ol300778e

文献信息

• N-Alkylation of Imidazoles with Dialkyl and Alkylene Carbonates
  作者：I. S. Gabov、L. A. Khamidullina、I. S. Puzyrev、M. A. Ezhikova、M. I. Kodess、A. V. Pestov

  DOI：10.1134/s1070428020120052

  日期：2020.12

  dialkyl and alkylene carbonates afforded the corresponding N-alkyl- and N-(hydroxyalkyl)imidazoles with high yields. The reactivity of dialkyl carbonates decreases in the series dimethyl > diethyl > dibutyl carbonate. Ethylene carbonate is a more efficient alkylating agent than trimethylene carbonate. The mechanisms of alkylation of imidazole with dimethyl carbonate and ethylene carbonate were studied

  咪唑与一系列碳酸二烷基酯和碳酸亚烷基酯的反应以高产率提供相应的 N-烷基-和 N-(羟烷基)咪唑。碳酸二烷基酯的反应性按碳酸二甲酯 > 二乙基 > 碳酸二丁酯的顺序降低。碳酸亚乙酯是比碳酸三亚甲基酯更有效的烷基化剂。通过DFT量子化学计算在B3LYP/6-311++G(d,p)理论水平上研究了咪唑与碳酸二甲酯和碳酸亚乙酯的烷基化机理。
• Phenethylthiazolylthiourea (PETT) Compounds as a New Class of HIV-1 Reverse Transcriptase Inhibitors. 2. Synthesis and Further Structure−Activity Relationship Studies of PETT Analogs
  作者：Amanda S. Cantrell、Per Engelhardt、Marita Högberg、S. Richard Jaskunas、Nils Gunnar Johansson、Christopher L. Jordan、Jussi Kangasmetsä、Michael D. Kinnick、Peter Lind、John M. Morin,、M. A. Muesing、Rolf Noreén、Bo Öberg、Paul Pranc、Christer Sahlberg、Robert J. Ternansky、Robert T. Vasileff、Lotta Vrang、Sarah J. West、Hong Zhang

  DOI：10.1021/jm950639r

  日期：1996.1.1

  Phenylethylthiazolylthiourea (PETT) derivatives have been identified as a new series of non-nucleoside inhibitors of HIV-1 RT. Structure-activity relationship studies of this class of compounds resulted in the identification of N-[2-(2-pyridyl)ethyl]-N'-[2-(5-bromopyridyl)]-thiourea hydrochloride (trovirdine; LY300046.HCl) as a highly potent anti-HIV-1 agent. Trovirdine is currently in phase one clinical

  苯乙基噻唑基硫脲（PETT）衍生物已被鉴定为HIV-1 RT的一系列新的非核苷抑制剂。此类化合物的构效关系研究确定了N- [2-（2-吡啶基）乙基] -N'-[2-（5-溴吡啶基）]-硫脲盐酸盐（卓维定； LY300046.HCl）作为高效的抗HIV-1药物。Trovirdine目前正处于一期临床试验中，有望用于治疗AIDS。正在扩展这些结构-活性关系研究以鉴定该系列中具有改进性能的其他化合物。这里描述了这项工作的一部分。研究了各种取代或未取代的杂芳族环取代PETT化合物的两个芳族部分。此外，还研究了苯环上多重取代的影响。在细胞培养测定中，对野生型和构建的HIV-1 RT突变体以及野生型HIV-1及其衍生的突变病毒Ile100和Cys181测定了抗病毒活性。在双突变病毒HIV-1（Ile 100 / Asn103）和HIV-1（Ile100 / Cys181）上确定了一些选定的化合物。合成
• [EN] FUSED IMIDAZOLE DERIVATIVES AS TGF-BETA INHIBITORS<br/>[FR] DÉRIVÉS IMIDAZOLES FUSIONNÉS POUVANT ÊTRE UTILISÉS COMME INHIBITEURS DU TGF-BETA
  申请人：RIGEL PHARMACEUTICALS INC

  公开号：WO2016081364A1

  公开（公告）日：2016-05-26

  Disclosed are imidazole compounds, as well as pharmaceutical compositions and methods of use thereof. One embodiment is a compound having the structure Formula (I) and pharmaceutically acceptable salts, prodrugs and N-oxides thereof (and solvates and hydrates thereof), wherein A, Z, X, R1, R2 m, p and a are as described herein. In certain embodiments, a compound disclosed herein inhibits TGF-β, and can be used to treat disease by blocking TGF-β signaling.

  本文披露了咪唑化合物，以及其药物组合物和使用方法。其中一种实施例是具有结构式（I）的化合物及其药用可接受的盐、前药和N-氧化物（以及其溶剂和水合物），其中A、Z、X、R1、R2、m、p和a如本文所述。在某些实施例中，本文披露的化合物抑制TGF-β，并可用于通过阻断TGF-β信号传导来治疗疾病。
• NOVEL COMPOUNDS HAVING cGMP-PDE INHIBITORY EFFECT
  申请人：MOCHIDA PHARMACEUTICAL CO., LTD.

  公开号：EP1048666A1

  公开（公告）日：2000-11-02

  Novel fused tetracyclic heterocyclic compounds having a potent and highly selective effect of inhibiting cyclic GMP phosphodiesterase (cGMP-PDE) and a high safety; a process for producing the same; drugs characterized by containing at least one of these compounds as the active ingredient, in particular, preventives and/or remedies for pulmonary hypertension, ischemic heart diseases, erectile insufficiency, female sexual dysfunction or diseases against which cGMP-PDE inhibitory effects are efficacious and intermediates useful in producing the above compounds.

  新型融合四环杂环化合物，具有抑制环 GMP 磷酸二酯酶（cGMP-PDE）的强效和高选择性作用，且安全性高；其生产工艺；以含有至少一种上述化合物作为活性成分为特征的药物，特别是肺动脉高压、缺血性心脏病、勃起功能障碍、女性性功能障碍或 cGMP-PDE 抑制作用有效的疾病的预防和/或治疗药物，以及用于生产上述化合物的中间体。
• Chemical mechanical polishing aqueous dispersion and chemical mechanical polishing method
  申请人：JSR Corporation

  公开号：EP1586614A1

  公开（公告）日：2005-10-19

  Disclosed is a chemical mechanical polishing aqueous dispersion comprising (A1) first fumed silica having a specific surface area of not less than 10 m2/g and less than 160 m2/g and an average secondary particle diameter of not less than 170 nm and not more than 250 nm and (A2) second fumed silica having a specific surface area of not less than 160 m2/g and an average secondary particle diameter of not less than 50 nm and less than 170 nm. Also disclosed is a chemical mechanical polishing method using the chemical mechanical polishing aqueous dispersion. According to the chemical mechanical polishing aqueous dispersion and the chemical mechanical polishing method, a chemical mechanical polishing process wherein a barrier metal layer and a cap layer can be efficiently removed by polishing and damage to an insulating film material of a low dielectric constant present in the underlying layer is reduced can be carried out.

  公开了一种化学机械抛光水性分散液，该分散液包含（A1）比表面积不小于 10 m2/g 且小于 160 m2/g、平均二次颗粒直径不小于 170 nm 且不大于 250 nm 的第一气相法二氧化硅；（A2）比表面积不小于 160 m2/g、平均二次颗粒直径不小于 50 nm 且小于 170 nm 的第二气相法二氧化硅。还公开了一种使用化学机械抛光水分散液的化学机械抛光方法。根据该化学机械抛光水性分散液和化学机械抛光方法，可进行化学机械抛光工艺，其中通过抛光可有效去除阻挡金属层和盖层，并减少对存在于底层中的低介电常数绝缘膜材料的损坏。