4-(2,5-二甲基-吡-1-基)苯甲酰肼 | 26165-67-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 4-(2,5-二甲基-吡-1-基)苯甲酰肼
• 中文别名: 4-(2,5-二甲基-吡-1-基）苯甲酸肼
• 英文名称: 4-(2,5-dimethylpyrrol-1-yl)benzoic acid hydrazide
• 英文别名: 4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoic acid hydrazide；4-(2,5-Dimethyl-1H-pyrrol-1-yl)benzohydrazide；4-(2,5-dimethylpyrrol-1-yl)benzohydrazide
• CAS: 26165-67-3
• 化学式: C₁₃H₁₅N₃O
• mdl: MFCD01570907
• 分子量: 229.282
• InChiKey: HJLBBIMOIDHHIB-UHFFFAOYSA-N

物化性质

• 熔点：
  168 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 海关编码：
  2933990090

SDS

Name:	4-(2 5-Dimethyl-1h-pyrrol-1-yl)benzohydrazide 97% Material Safety Data Sheet
Synonym:
CAS:	26165-67-3

Section 1 - Chemical Product MSDS Name:4-(2 5-Dimethyl-1h-pyrrol-1-yl)benzohydrazide 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
26165-67-3	4-(2,5-Dimethyl-1H-pyrrol-1-yl)benzohy	97%	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.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 26165-67-3: 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: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 168 - 169 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: C13H15N3O
Molecular Weight: 229

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, acrid smoke and fumes.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 26165-67-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-(2,5-Dimethyl-1H-pyrrol-1-yl)benzohydrazide - 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# 26165-67-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 26165-67-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 26165-67-3 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

反应信息

• 作为反应物：
  描述：

  4-(2,5-二甲基-吡-1-基)苯甲酰肼 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 4-allyl-3-[4-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl]-1H-1,2,4-triazole-5-thione
  参考文献：
  名称：

  3-巯基-1,2,4-三唑-吡咯杂种的抗分枝杆菌活性的设计，合成和评估

  摘要：

  通过使用5-（4-（1（$ H $-吡咯-1-基）苯基）-4 $ H $- 1,2,4-三唑-3-硫醇作为支架，在N-4和N-2的三唑环上引入了几种类型的部分，并作为巯基的取代基。前述部分是N-4处的烯丙基或苯基部分；N-2处的氨基甲基；或在硫上的甲基，取代的苄基，乙氧基羰基甲基或取代的苯甲酰基。在所得文库中作为耻垢分枝杆菌生长抑制剂的化合物的研究表明，其最低抑菌浓度高于64 mg / L。

  DOI：

  10.3906/kim-1811-4
• 作为产物：
  描述：

  4-(2,5-二甲基吡咯-1-基)苯甲酸 在 盐酸 、 一水合肼 作用下， 生成 4-(2,5-二甲基-吡-1-基)苯甲酰肼
  参考文献：
  名称：

  设计，合成，分子对接和3D-QSAR研究作为潜在抗分枝杆菌药的强力烯酰基酰基载体蛋白还原酶抑制剂

  摘要：

  为了开发抗结核分枝杆菌的先导化合物，已合成和筛选了一系列针对必需的烯酰-ACP还原酶的52种新颖的吡咯肼衍生物。采用表面对接法研究了化合物在烯酰-ACP还原酶活性位点的结合方式。结合模型表明吡咯和InhA酶之间有一个或两个氢键相互作用。高活性化合物5r（MIC 0.2μg/ mL）显示与Tyr158和NAD +的氢键相互作用以与配体PT70和三氯生相同的方式。就整体统计而言，通过数据库对齐生成的CoMFA和CoMSIA模型是最好的。CoMFA和CoMSIA模型的预测能力是使用13种化合物的测试集确定的，其预测相关系数（r pred 2）分别为0.896和0.930。

  DOI：

  10.1016/j.ejmech.2013.11.004

文献信息

• Synthesis, characterization, biological activity, and 3D-QSAR studies on some novel class of pyrrole derivatives as antitubercular agents
  作者：Shrinivas D. Joshi、Uttam A. More、Sheshagiri R. Dixit、Haresh H. Korat、Tejraj M. Aminabhavi、Aravind M. Badiger

  DOI：10.1007/s00044-013-0709-y

  日期：2014.3

  designed, synthesized, and their structures have been elucidated along with the evaluation of antitubercular activity against Mycobacterium tuberculosis H37Rv using the microplate alamar blue assay method and antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Klebsiella pneumoniae, and Escherichia coli by broth micro-dilution assay method. Structural activity relationships and 3D-QSAR

  摘要设计，合成了一系列新的吡咯衍生物，并阐明了它们的结构，并使用微孔板阿拉玛蓝法评估了其对结核分枝杆菌H 37 Rv的抗结核活性以及对金黄色葡萄球菌，枯草芽孢杆菌，肺炎克雷伯菌的抗菌活性，以及通过肉汤微稀释法测定的大肠杆菌。结构活性关系和3D-QSAR分析已通过拓扑异构体比较分子场分析（CoMFA）进行。使用42个训练集和8个活性化合物的测试集来开发显示交叉验证相关系数（q 2）为0.815，预测标准误差为0.36，非交叉验证相关系数（r 2）为0.973，六项估计的标准误差为0.14。 图形概要合成; 频谱和3D-QSAR研究；描述了一系列新颖的吡咯衍生物的抗细菌，抗结核和细胞毒性活性。
• Synthesis, characterization and antitubercular activities of novel pyrrolyl hydrazones and their Cu-complexes
  作者：Shrinivas D. Joshi、Devendra Kumar、Sheshagiri R. Dixit、Nageshwar Tigadi、Uttam A. More、Christian Lherbet、Tejraj M. Aminabhavi、Kap Seung Yang

  DOI：10.1016/j.ejmech.2016.05.025

  日期：2016.10

  Novel pyrrolyl hydrazones and their copper complexes have been synthesized and characterized using analytical and spectral techniques to show the tetrahedral geometry for Cu(II) complexes. Biological activities of hydrazones have been assessed to understand the role of metal ion on their biological activity and the effect of pyrrolyl hydrazones. In vitro antitubercular activity against Mycobacterium

  合成了新型吡咯基hydr及其铜配合物，并使用分析和光谱技术对其进行了表征，以显示Cu（II）配合物的四面体几何形状。评估了hydr的生物活性，以了解金属离子对其生物学活性的作用以及吡咯基的作用。对金属配合物（13b和13r的结核分枝杆菌）的体外抗结核活性）表现出最高的抗结核活性，非常接近利福平（0.4μg/ mL），MIC为0.8μg/ mL。所有其他化合物均显示出良好的活性，MIC值为1.6至100μg/ mL。配体及其配合物的抑制值的比较研究表明，配合物的抗菌活性高于配体。一些化合物对InhA具有良好的活性，尤其是化合物12r，13b和13r甚至在5μM时仍显示出与酶的60％以上的结合（显示出高达2.4μM的良好IC50）。大多数活性分子对人肺癌细胞系A549的细胞毒性非常小。已经进行了对接和3D-QSAR研究，以提供有关此类化合物作用机理的一些见解。
• Cascade Synthesis of Pyrroles from Nitroarenes with Benign Reductants Using a Heterogeneous Cobalt Catalyst
  作者：Pavel Ryabchuk、Thomas Leischner、Carsten Kreyenschulte、Anke Spannenberg、Kathrin Junge、Matthias Beller

  DOI：10.1002/anie.202007613

  日期：2020.10.12

  A bifunctional 3d‐metal catalyst for the cascade synthesis of diverse pyrroles from nitroarenes is presented. The optimal catalytic system Co/NGr‐C@SiO2‐L is obtained by pyrolysis of a cobalt‐impregnated composite followed by subsequent selective leaching. In the presence of this material, (transfer) hydrogenation of easily available nitroarenes and subsequent Paal–Knorr/Clauson‐Kass condensation provides

  提出了一种用于从硝基芳烃级联合成多种吡咯的双功能3d金属催化剂。最佳催化体系Co/NGr-C@SiO 2 -L是通过热解钴浸渍复合材料并随后进行选择性浸出而获得的。在这种材料的存在下，容易获得的硝基芳烃的（转移）氢化和随后的 Paal-Knorr/Clauson-Kass 缩合可使用二氢、甲酸或 CO/H 2 O混合物（WGSR条件）作为还原剂。除了有利的步骤经济性之外，这种简单的多米诺骨牌工艺不需要任何溶剂或外部助催化剂。该方法的一般合成效用在各种功能化底物上得到了证明，包括生物活性和药学相关化合物的制备，例如（+）-异沙莫坦。
• Synthesis of new 4-(2,5-dimethylpyrrol-1-yl)/4-pyrrol-1-yl benzoic acid hydrazide analogs and some derived oxadiazole, triazole and pyrrole ring systems: a novel class of potential antibacterial, antifungal and antitubercular agents
  作者：S. D. Joshi、Yogesh More、H. M. Vagdevi、V. P. Vaidya、G. S. Gadaginamath、V. H. Kulkarni

  DOI：10.1007/s00044-012-0112-0

  日期：2013.3

  values 1–4 μg mL−1. Several compounds 4, 8d, 9, 12c–d and 12f–h exhibited good in vitro antitubercular activity with MIC values 1–2 μg mL−1. Further, some title compounds were also assessed for their cytotoxic activity (IC50) against mammalian Vero cell lines and A549 (lung adenocarcinoma) cell lines using MTT assay method. The results reveal that these compounds exhibit antitubercular activity at non-cytotoxic

  摘要一系列4-（2,5-二甲基吡咯-1-基）/ 4-吡咯-1-基苯甲酸酰肼类似物，一些衍生的1,3,4-恶二唑，5-取代的-4-氨基-1,2合成了高产率的1，4-三唑啉-3-硫酮和2，5-二甲基吡咯，并通过IR，1 H NMR，13 C NMR，质谱和元素分析确定了这些化合物的结构。通过肉汤稀释法评价这些化合物对结核分枝杆菌H 37 Rv菌株的初步体外抗菌，抗真菌和抗结核活性。这些化合物中的十二种显示出良好的抗菌活性，最小抑菌浓度（MIC）值为1-4μgmL -1。几种化合物4，8D，9，12C - d和12F - ħ体外抗结核活性显示出良好的与MIC值1-2微克毫升-1。此外，还使用MTT测定法评估了一些标题化合物对哺乳动物Vero细胞系和A 549（肺腺癌）细胞系的细胞毒活性（IC 50）。结果表明，这些化合物在非细胞毒性浓度下具有抗结核活性。 图形概要描述了一系列新型吡咯衍生物的合成，光谱研究以及抗菌，抗真菌和抗结核活性
• Chloramine Trihydrate‐Mediated Tandem Synthesis of New Pyrrole and/or Arene‐Linked Mono‐ and Bis(1,3,4‐Oxadiazole) Hybrids as Potential Bacterial Biofilm and MRSA Inhibitors
  作者：Ahmed E. M. Mekky、Tamer T. El‐Idreesy、Sherif M. H. Sanad

  DOI：10.1002/cbdv.202200338

  日期：2022.8

  against MRSA ATCC : 33591, and ATCC : 43300 strains, with MIC, and MBC values ranging from 3.8–7.9 and 7.7–15.8 μM, respectively. When tested against the MCF-10A cell lines, hybrids 11c, and 11f are cytotoxic at concEntrations that are more than 6 and 13-fold higher than their MIC values against the S. aureus, E. coli, and P. aeruginosa strains, respectively. This lends support to both hybrids′ potential

  使用两步串联方案制备新的吡咯和/或芳烃连接的双 (1,3,4-恶二唑) 及其单类似物。适当的醛和苯甲酰肼首先在乙醇中在 80 °C 下缩合，得到相应的N-苯甲酰腙。在没有分离的情况下，先前的中间体在 180°C 下在 DMSO 中进行三水合氯胺介导的氧化环化以产生目标分子。（吡咯-芳烃）连接的杂种的抗菌效力超过了芳烃连接的杂种，双（1,3,4-恶二唑）对六种不同的ATCC菌株超过了它们的单类似物。此外，与吡咯有关的双( 1,3,4-恶二唑) 11c和11f的抗菌效力甲苯硫基）甲基单位对金黄色葡萄球菌、大肠杆菌和铜绿假单胞菌菌株的影响最高。它们的 MIC 介于 3.8 和 3.9 μM 之间，而它们的 MBC 值介于 7.7 和 15.8 μM 之间。此外，它们对测试的相同菌株显示出有希望的细菌生物膜抑制活性，IC 50值范围为 4.7 至 5.3 μM。它们对 MRSA ATCC : 33591