(5-(2-噻吩基)异噁唑)甲醇 | 194491-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: (5-(2-噻吩基)异噁唑)甲醇
• 中文别名: 5-(2-噻吩基)异恶唑)甲醇
• 英文名称: (5-(thiophen-2-yl)isoxazol-3-yl)methanol
• 英文别名: 5-(2-thienyl)-3-isoxazolecarbaldehyde；[5-(2-thienyl)isoxazol-3-yl]methanol；[5-(2-Thienyl)-3-isoxazolyl]methanol；(5-thiophen-2-yl-1,2-oxazol-3-yl)methanol
• CAS: 194491-44-6
• 化学式: C₈H₇NO₂S
• 分子量: 181.215
• InChiKey: HUAGDHXVPCSWLD-UHFFFAOYSA-N

物化性质

• 熔点：
  54-55
• 沸点：
  366.0±32.0 °C(Predicted)
• 密度：
  1.351±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C，避光干燥

SDS

Name:	[5-(2-Thienyl)-3-isoxazolyl]methanol tech Material Safety Data Sheet
Synonym:
CAS:	194491-44-6

Section 1 - Chemical Product MSDS Name:[5-(2-Thienyl)-3-isoxazolyl]methanol tech Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
194491-44-6	[5-(2-Thienyl)-3-isoxazolyl]methanol		unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Store under nitrogen.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 194491-44-6: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 54 - 55 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H7NO2S
Molecular Weight: 181.21

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents, acids, acid chlorides, halogenated agents, halogens.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 194491-44-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
[5-(2-Thienyl)-3-isoxazolyl]methanol - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 194491-44-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 194491-44-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 194491-44-6 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化合物D，即[5)-(2-噻吩基)-3-异唑甲醇，是一种AgrA-DNA结合抑制剂，并且可用于研究金黄色葡萄球菌感染。

反应信息

• 作为反应物：
  描述：

  (5-(2-噻吩基)异噁唑)甲醇 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到5-(2-噻吩基)-3-异噁唑甲醛
  参考文献：
  名称：

  Xa因子活性位点的分子识别：阳离子-π相互作用，平面肽表面堆积和结构水的置换

  摘要：

  Xa因子是一种来自凝血级联的丝氨酸蛋白酶，是分子识别研究的理想酶，因为其活性位点具有高度的形状持久性，并具有独特的凹子口袋。我们开发了一系列非肽小分子抑制剂，这些抑制剂具有中心三环核，该核将中性杂环取代基定向到S1袋中，并将季铵离子定向到S4袋中的芳族盒中。系统地改变了取代基的种类，以研究S4口袋中的阳离子与π相互作用，S1口袋内衬的扁平肽壁上的最佳杂环堆积以及S1和S4口袋中的潜在水替代物。建立了构效关系，以揭示和量化对结合自由焓的贡献，由单原子替换或配体位置变化引起的。一系列高亲和力配体，抑制常数低至获得了K i = 2 n M，并通过蛋白质-配体复合物的X射线共晶体结构证实了其拟定的结合几何形状。

  DOI：

  10.1002/chem.201102571
• 作为产物：
  描述：

  2,4-二氧代-4-(2-噻吩)丁酸乙酯 在 sodium tetrahydroborate 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 (5-(2-噻吩基)异噁唑)甲醇
  参考文献：
  名称：

  Xa因子活性位点的分子识别：阳离子-π相互作用，平面肽表面堆积和结构水的置换

  摘要：

  Xa因子是一种来自凝血级联的丝氨酸蛋白酶，是分子识别研究的理想酶，因为其活性位点具有高度的形状持久性，并具有独特的凹子口袋。我们开发了一系列非肽小分子抑制剂，这些抑制剂具有中心三环核，该核将中性杂环取代基定向到S1袋中，并将季铵离子定向到S4袋中的芳族盒中。系统地改变了取代基的种类，以研究S4口袋中的阳离子与π相互作用，S1口袋内衬的扁平肽壁上的最佳杂环堆积以及S1和S4口袋中的潜在水替代物。建立了构效关系，以揭示和量化对结合自由焓的贡献，由单原子替换或配体位置变化引起的。一系列高亲和力配体，抑制常数低至获得了K i = 2 n M，并通过蛋白质-配体复合物的X射线共晶体结构证实了其拟定的结合几何形状。

  DOI：

  10.1002/chem.201102571

文献信息

• Novel N-Substituted oseltamivir derivatives as potent influenza neuraminidase inhibitors: Design, synthesis, biological evaluation, ADME prediction and molecular docking studies
  作者：Jiqing Ye、Xiao Yang、Min Xu、Paul Kay-sheung Chan、Cong Ma

  DOI：10.1016/j.ejmech.2019.111635

  日期：2019.11

  strain. Moreover, the in silico ADME predictions showed that the selected compounds had comparable properties with oseltamivir carboxylate, which demonstrated the druggablity of these derivatives. Furthermore, molecular docking studies showed that the most potent compound 6f and 10i could adopt different modes of binding interaction with NA, which may provide novel solutions for treating oseltamivir-resistant

  新型有效的神经氨酸酶（NA）抑制剂的发现仍然是治疗由流感引起的传染病的有吸引力的方法。在这项研究中，我们描述了新型的N-取代的奥司他韦衍生物的设计和合成，以探测与NA的活性位有关的150腔。NA抑制研究表明，新衍生物显示出对临床流感病毒株NA的抑制活性，IC50值为nM。此外，计算机模拟ADME的预测结果表明，所选化合物与oseltamivir羧酸盐具有可比的特性，这证明了这些衍生物的药物相容性。此外，分子对接研究表明，最有效的化合物6f和10i可以采用与NA相互作用的不同模式，可能为治疗耐奥司他韦的流感提供新颖的解决方案。根据研究结果，我们认为化合物6f和10i作为新型抗病毒药物具有进一步研究的潜力。
• [EN] PYRADAZINONE DERIVATIVES AND THE COMPOSITIONS AND METHODS OF TREATMENT REGARDING THE SAME<br/>[FR] DÉRIVÉS DE PYRADAZINONE ET COMPOSITIONS ET PROCÉDÉS DE TRAITEMENT ASSOCIÉS
  申请人：AN2H DISCOVERY LTD

  公开号：WO2017210685A1

  公开（公告）日：2017-12-07

  The present disclosure is directed to pyridazin-3(2H)-one compounds of formula (I), pharmaceutical compositions thereof and methods for modulating or activating a Parkin ligase The present disclosure is also directed to methods of treating and/or reducing the incidence of diseases or conditions related to the activation of Parkin ligase, R21, R22, R23, R24 and R25 are as defined herein.

  本公开涉及式(I)的吡啶并嗪-3(2H)-酮化合物，其药物组成以及调节或激活帕金连接酶的方法。本公开还涉及治疗和/或减少与帕金连接酶激活相关的疾病或病况的方法，其中R21、R22、R23、R24和R25如本文所定义。
• Radical chlorination of non-resonant heterobenzylic C‒H bonds and high-throughput diversification of heterocycles
  作者：Dung L. Golden、Kaitlyn M. Flynn、Santeri Aikonen、Christopher M. Hanneman、Dipannita Kalyani、Shane W. Krska、Robert S. Paton、Shannon S. Stahl

  DOI：10.1016/j.chempr.2024.04.001

  日期：2024.4

  Site-selective functionalization of the heterobenzylic C(sp)–H bonds of pyridines and related heteroaromatic compounds presents challenges associated with the basic nitrogen atom and the variable reactivity among different positions on the heteroaromatic ring. Methods for functionalization of 2- and 4-alkylpyridines are increasingly available through polar pathways that leverage resonance stabilization

  吡啶和相关杂芳族化合物的杂苄基 C(sp)-H 键的位点选择性官能化提出了与碱性氮原子和杂芳环上不同位置之间的可变反应性相关的挑战。 2-和4-烷基吡啶的功能化方法越来越多地通过利用这些位置上电荷积累的共振稳定性的极性途径来实现。相比之下，3-烷基吡啶的官能化基本上是难以实现的。在这里，我们报道了一种光化学促进的方法，用于 3-烷基吡啶和相关烷基杂芳烃中非共振杂苄基 C(sp)-H 位点的氯化。密度泛函理论计算表明，最佳反应性反映了两个自由基链增长步骤的能量之间的平衡，优选试剂由β-氯磺酰胺组成。操作简单的氯化方案能够获得杂苄基氯化物，它可作为杂芳族结构单元和各种氧化敏感亲核试剂之间的 C-H 交叉偶联反应的多功能中间体，通过高通量实验进行。
• Identification of small-molecule inhibitors of USP2a
  作者：Marcin D. Tomala、Katarzyna Magiera-Mularz、Katarzyna Kubica、Sylwia Krzanik、Bartosz Zieba、Bogdan Musielak、Marcin Pustula、Grzegorz M. Popowicz、Michael Sattler、Grzegorz Dubin、Lukasz Skalniak、Tad A. Holak

  DOI：10.1016/j.ejmech.2018.03.009

  日期：2018.4

  USP2a is a deubiquitinating protease that rescues its target proteins from destruction by the proteasome by reversing the process of protein ubiquitination. USP2a shows oncogenic properties in vivo and has been found to be a specific activator of cyclin D1. Many types of cancers are addicted to cyclin D1 expression. Targeting USP2a is a promising strategy for cancer therapy but little progress has been made in the field of inhibition of USP2a. Using NMR-based fragment screening and biophysical binding assays, we have discovered small molecules that bind to USP2a. Iterations of fragment combination and structure-driven design identified two 5-(2-thienyl)-3-isoxazoles as the inhibitors of the USP2a-ubiquitin protein-protein interaction. The affinity of these molecules for the catalytic domain of USP2a parallels their ability to interfere with USP2a binding to ubiquitin in vitro. Altogether, our results establish the 5(2-thienyl)-3-isoxazole pharmacophore as an attractive starting point for lead optimization. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Molecular Recognition at the Active Site of Factor Xa: Cation-π Interactions, Stacking on Planar Peptide Surfaces, and Replacement of Structural Water
  作者：Laura M. Salonen、Mareike C. Holland、Philip S. J. Kaib、Wolfgang Haap、Jörg Benz、Jean-Luc Mary、Olivier Kuster、W. Bernd Schweizer、David W. Banner、François Diederich

  DOI：10.1002/chem.201102571

  日期：2012.1.2

  and features distinct, concave sub‐pockets. We developed a family of non‐peptidic, small‐molecule inhibitors with a central tricyclic core orienting a neutral heterocyclic substituent into the S1 pocket and a quaternary ammonium ion into the aromatic box in the S4 pocket. The substituents were systematically varied to investigate cation–π interactions in the S4 pocket, optimal heterocyclic stacking on

  Xa因子是一种来自凝血级联的丝氨酸蛋白酶，是分子识别研究的理想酶，因为其活性位点具有高度的形状持久性，并具有独特的凹子口袋。我们开发了一系列非肽小分子抑制剂，这些抑制剂具有中心三环核，该核将中性杂环取代基定向到S1袋中，并将季铵离子定向到S4袋中的芳族盒中。系统地改变了取代基的种类，以研究S4口袋中的阳离子与π相互作用，S1口袋内衬的扁平肽壁上的最佳杂环堆积以及S1和S4口袋中的潜在水替代物。建立了构效关系，以揭示和量化对结合自由焓的贡献，由单原子替换或配体位置变化引起的。一系列高亲和力配体，抑制常数低至获得了K i = 2 n M，并通过蛋白质-配体复合物的X射线共晶体结构证实了其拟定的结合几何形状。