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3,4,5-Trimethoxybenzhydrazide is an organic compound characterized by its unique chemical structure, which features a benzene ring with three methoxy groups and a hydrazide functional group. 3,4,5-Trimethoxybenzhydrazide is known for its potential applications in various fields due to its distinct properties.

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  • 3291-03-0 Structure
  • Basic information

    1. Product Name: 3,4,5-TRIMETHOXYBENZHYDRAZIDE
    2. Synonyms: LABOTEST-BB LT00454860;3,4,5-TRIMETHOXYBENZOHYDRAZIDE;3,4,5-TRIMETHOXYBENZOIC ACID HYDRAZIDE;3,4,5-TRIMETHOXYBENZOIC HYDRAZIDE;3,4,5-TRIMETHOXYBENZENE-1-CARBOHYDRAZIDE;3,4,5-TRIMETHOXYBENZHYDRAZIDE;AKOS AU36-M150;AKOS BBS-00001045
    3. CAS NO:3291-03-0
    4. Molecular Formula: C10H14N2O4
    5. Molecular Weight: 226.23
    6. EINECS: 221-954-6
    7. Product Categories: Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes
    8. Mol File: 3291-03-0.mol
  • Chemical Properties

    1. Melting Point: 158-160°C
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.197
    6. Refractive Index: 1.534
    7. Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
    8. Solubility: N/A
    9. PKA: 11.78±0.10(Predicted)
    10. BRN: 484531
    11. CAS DataBase Reference: 3,4,5-TRIMETHOXYBENZHYDRAZIDE(CAS DataBase Reference)
    12. NIST Chemistry Reference: 3,4,5-TRIMETHOXYBENZHYDRAZIDE(3291-03-0)
    13. EPA Substance Registry System: 3,4,5-TRIMETHOXYBENZHYDRAZIDE(3291-03-0)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36/37/39
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 3291-03-0(Hazardous Substances Data)

3291-03-0 Usage

Uses

Used in Photochromic and Fluorescent Applications:
3,4,5-Trimethoxybenzhydrazide is used as a key compound in the preparation of materials with photochromic and fluorescent properties. Its unique chemical structure allows it to undergo reversible changes in response to light, making it a valuable component in the development of advanced materials for various applications.
Used in Chemical Synthesis:
3,4,5-Trimethoxybenzhydrazide is also utilized as an intermediate in the synthesis of various organic compounds. Its versatile structure enables it to be a building block for the creation of a wide range of molecules with different functionalities and applications.
Used in Research and Development:
Due to its unique properties and potential applications, 3,4,5-Trimethoxybenzhydrazide is often employed in research and development efforts to explore new materials, chemical reactions, and potential uses in various industries.

Check Digit Verification of cas no

The CAS Registry Mumber 3291-03-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,2,9 and 1 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 3291-03:
(6*3)+(5*2)+(4*9)+(3*1)+(2*0)+(1*3)=70
70 % 10 = 0
So 3291-03-0 is a valid CAS Registry Number.
InChI:InChI=1/C10H14N2O4/c1-14-7-4-6(10(13)12-11)5-8(15-2)9(7)16-3/h4-5H,11H2,1-3H3,(H,12,13)

3291-03-0 Well-known Company Product Price

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  • Alfa Aesar

  • (B20055)  3,4,5-Trimethoxybenzhydrazide, 98%   

  • 3291-03-0

  • 5g

  • 716.0CNY

  • Detail
  • Alfa Aesar

  • (B20055)  3,4,5-Trimethoxybenzhydrazide, 98%   

  • 3291-03-0

  • 25g

  • 1679.0CNY

  • Detail

3291-03-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 3,4,5-trimethoxybenzohydrazide

1.2 Other means of identification

Product number -
Other names 1,2,3-trimethoxybenzene-5-carbohydrazide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3291-03-0 SDS

3291-03-0Relevant articles and documents

LASSBio-1586, an N-acylhydrazone derivative, attenuates nociceptive behavior and the inflammatory response in mice

Silva, Juliane Cabral,De Oliveira, Raimundo Gon?alves,e Silva, Mariana Gama,De Lavor, érica Martins,Soares, Juliana Mikaelly Dias,De Lima-Saraiva, Sarah Raquel Gomes,Diniz, Tamara Coimbra,Mendes, Rosemairy Luciane,De Alencar Filho, Edilson Beserra,De Lacerda Barreiro, Eliezer Jesus,Lima, Lídia Moreira,Da Silva Almeida, Jackson Roberto Guedes

, (2018)

Pain and inflammation are complex clinical conditions that are present in a wide variety of disorders. Most drugs used to treat pain and inflammation have potential side effects, which makes it necessary to search for new sources of bioactive molecules. In this paper, we describe the ability of LASSBio-1586, an N-acylhydrazone derivative, to attenuate nociceptive behavior and the inflammatory response in mice. Antinociceptive activity was evaluated through acetic acid-induced writhing and formalin-induced nociception tests. In these experimental models, LASSBio-1586 significantly (p0.05) reduced nociceptive behavior. Several methods of acute and chronic inflammation induced by different chemical (carrageenan, histamine, croton oil, arachidonic acid) and physical (cotton pellet) agents were used to evaluate the anti-inflammatory effect of LASSBio-1586. LASSBio-1586 exhibited potent anti-inflammatory activity in all tests (p0.05). Study of the mechanism of action demonstrated the possible involvement of the nitrergic, serotonergic and histamine signaling pathways. In addition, a molecular docking study was performed, indicating that LASSBio-1586 is able to block the COX-2 enzyme, reducing arachidonic acid metabolism and consequently decreasing the production of prostaglandins, which are important inflammatory mediators. In summary, LASSBio-1586 exhibited relevant antinociceptive and anti-inflammatory potential and acted on several targets, making it a candidate for a new multi-target oral anti-inflammatory drug.

Synthesis, biological evaluation, and structure-activity relationships of new tubulin polymerization inhibitors based on 5-amino-1,2,4-triazole scaffold

Yang, Fang,Chen, Lin,Lai, Jin-Mei,Jian, Xie-Er,Lv, Dong-Xin,Yuan, Li-Li,Liu, Yu-Xia,Liang, Feng-Ting,Zheng, Xiao-Lan,Li, Xiong-Li,Wei, Li-Yuan,You, Wen-Wei,Zhao, Pei-Liang

, (2021/03/06)

Based on our previous research, thirty new 5-amino-1H-1,2,4-triazoles possessing 3,4,5-trimethoxyphenyl moiety were synthesized, and evaluated for antiproliferative activities. Among them, compounds IIa, IIIh, and IIIm demonstrated significant antiproliferative activities against a panel of tumor cell lines, and the promising compound IIIm dose-dependently caused G2/M phase arrest in HeLa cells. Furthermore, analogue IIa exhibited the most potent tubulin polymerization inhibitory activity with an IC50 value of 9.4 μM, and molecular modeling studies revealed that IIa formed stable interactions in the colchicine-binding site of tubulin, suggesting that 5-amino-1H-1,2,4-triazole scaffold has potential for further investigation to develop novel tubulin polymerization inhibitors with anticancer activity.

Discovery of highly potent tubulin polymerization inhibitors: Design, synthesis, and structure-activity relationships of novel 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidines

Huo, Xian-Sen,Jian, Xie-Er,Ou-Yang, Jie,Chen, Lin,Yang, Fang,Lv, Dong-Xin,You, Wen-Wei,Rao, Jin-Jun,Zhao, Pei-Liang

, (2021/05/10)

By removing 5-methyl and 6-acetyl groups in our previously reported compound 3, we designed a series of novel 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidine derivatives as potential tubulin polymerization inhibitors. Among them, compound 5e displayed low nanomolar antiproliferative efficacy on HeLa cells which was 166-fold higher than the lead analogue 3. Interestingly, 5e displayed significant selectivity in inhibiting cancer cells over HEK-293 (normal human embryonic kidney cells). In addition, 5e dose-dependently arrested HeLa in G2/M phase through the alterations of the expression levels of p-cdc2 and cyclin B1, and caused HeLa cells apoptosis by regulation of expressions of cleaved PARP. Further evidence demonstrated that 5e effectively inhibited tubulin polymerization and was 3-fold more powerful than positive control CA-4. Moreover, molecular docking analysis indicated that 5e overlapped well with CA-4 in the colchicine-binding site. These studies demonstrated that 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidine skeleton might be used as the leading unit to develop novel tubulin polymerization inhibitors as potential anticancer agents.

Synthesis, characterization (theoretical and biological study) of some transition metal complexes with new schiff base derived from 1,2,4-triazole

AL-Jibouri, Mahmoud Najim,Jawad, Waleed A.,Balakit, Asim A.,Obies, Mohammed

, p. 5229 - 5241 (2021/08/31)

The present work involves, new Schiff base of (E)-2-(((3-mercapto-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazol-4-yl)imino)methyl)phenol (L2) has been synthesized by condensation reaction of 4-amino-5-(3,4,5 trimethoxy phenyl)-4H-1,2,4-triazole-3-thiol with 2-hydroxybenzaldehyde. The new Schiff base (L2) used as a ligand to synthesize a new complex with Co(II), Ni(II), Cu(II), Pd(II), and Cd(II) metal ions by 1:1 (Metal: ligand) ratio. New ligand and their complexes have been exanimated and confirmed by fourier-transform infrared (FT-IR), ultraviolet-visible (UV-visible), proton nuclear magnetic resonance (1HNMR), carbon13 nuclear magnetic resonance (13CNMR), microelement analysis (CHNS), thermal analysis (TG-DSC), atomic absorption flame (AAF), conductivity and magnetic susceptibility. The results obtained from spectra, elemental analyses and thermal analyses (TG-DSC) and compare by density functional theory (DFT) and TD-DFT calculations were screened for some selected complexes and the observed data indicated their stability and the expected chemical formula, Pd(II) were square planner, whereas the Cu(II), Co(II), Ni(II) octahedral, and Cd(II) were tetrahedral geometry . Furthermore, the antibacterial and antifungal activity was screened for the DMSO solution concerning the Schiff base (L2) and its complexes (20 μg/ml) against two kinds of gram; (Staphylococcus aureas and Bacillus subtilis) positive and two negative bacteria; (Esherichia coli and Burkholderia) and against (Candida albican) fungi. The results obtained from diffusion method confirmed the greater activity of Pd(II) and Cd(II) complexes whereas the Co(II),Cu(II) and Ni(II) complexes showed medium activity compared with the low inhibition zones of the free Schiff base of 1, 2, 4- triazole derivative.

Antibacterial and Antiviral Activities of 1,3,4-Oxadiazole Thioether 4H-Chromen-4-one Derivatives

Cao, Xiao,Liu, Fang,Liu, Liwei,Liu, Tingting,Peng, Feng,Wang, Qifan,Xie, Chengwei,Xue, Wei,Yang, Jinsong

, p. 11085 - 11094 (2021/10/01)

Various 1,3,4-oxadiazole thioether 4H-chromen-4-one derivatives were conceived. The title compounds demonstrated striking inhibitory effects againstXac,Psa, andXoo. EC50data exhibited that A8 (19.7 μg/mL) had better antibacterial activity againstXoothan myricetin, BT, and TC. Simultaneously, the mechanism of action of A8 had been verified by SEM. The results of anti-tobacco mosaic virus indicated that A9 had the bestin vivoantiviral effect compared with ningnanmycin. From the data of MST, it could be seen that A9 (0.003 ± 0.001 μmol/L) exhibited a strong binding capacity, which was far superior to ningnanmycin (2.726 ± 1.301 μmol/L). This study shows that the 1,3,4-oxadiazole thioether 4H-chromen-4-one derivatives may become agricultural drugs with great potential.

Molecular docking studies, biological evaluation and synthesis of novel 3-mercapto-1,2,4-triazole derivatives

Ghanaat, Javad,Khalilzadeh, Mohammad A.,Zareyee, Daryoush

, p. 223 - 232 (2020/02/25)

Abstract: Synthesis of bioactive heterocyclic compounds having effective biological activity is an essential research area for wide-ranging applications. In this study, a conventional methodology has been developed for the synthesis of a series of new 3-mercapto-1,2,4-triazole derivatives 4a–f. The purity and structure of the synthesized molecules were confirmed by 1H NMR, 13C NMR and elemental analysis. In addition, the prepared compounds were screened for their anti-proliferative activity against three human cancer cell lines including A549 (lung cancer), MCF7 (breast cancer) and SKOV3 (ovarian cancer) using MTT reduction assay. All the tested compounds demonstrated remarkable cytotoxic activity with IC50 values ranging from 3.02 to 15.37?μM. The heterocyclic compound bearing 3,4,5-trimethoxy moiety was found to be the most effective among the series displaying an IC50 of 3.02?μM specifically against the ovarian carcinoma cancer cell line (SKOV3). Moreover, Annexin V-FITC/propidium iodide staining assay indicated that this compound can induce apoptosis in SKOV3 cells. Furthermore, cell cycle assay showed a significant cell cycle arrest at the G2/M phase in a dose-dependent manner for this compound. The molecular docking results was showed binding modes of potent compound 4d perfectly corroborated the suggestion of binding to the colchicine site. The entire results conclude that 3-mercapto-1,2,4-triazole derivatives can be synthesized by a green method for biological and pharmacological applications. Graphic abstract: New analogs of 3-mercapto-1,2,4-triazole potential derivatives for anti-proliferative activity were synthesized. Cytotoxic activity of all synthesized compounds was evaluated against tree human cancer cell lines: lung (A549), breast (MCF7) and ovarian (SKOV3).[Figure not available: see fulltext.].

Design, synthesis, and biological evaluation of phenyloxadiazole derivatives as potential antifungal agents against phytopathogenic fungi

Li, Yitao,Yao, Wenqiang,Lin, Jian,Gao, Guoliang,Huang, Chang,Wu, Yang

, p. 121 - 135 (2021/01/05)

Abstract: A novel series of picarbutrazox-inspired oxadiazole hybrids was synthesized and the derivatives’ biological activity against phytopathogenic fungi was investigated. The molecules were designed by retaining the active fragment of tetrazolyl phenyloxime ether of lead compound picarbutrazox, while introducing the potentially active oxadiazole-derived fragment. Bioassay results revealed that some of the title compounds showed potent in vivo antifungal activities to control cucumber downy mildew. Therefore, this novel oxadiazole phenyloxadiazole derivative can be used as a potential antifungal agent to control cucumber downy mildew and other phytopathogenic fungi for crop protection. Graphic abstract: [Figure not available: see fulltext.].

HCK INHIBITORS FOR THE TREATMENT OF FIBROSIS AND CANCER

-

Paragraph 00103; 00106; 00108, (2020/10/20)

Compounds which are thiazole and triazole derivatives are disclosed, including compounds of the following genus: Formula I. The compounds are inhibitors of hematopoietic cell kinase (HCK) and exhibit anti-fibrotic and anti-proliferative effects. They are useful in the treatment of a variety of disorders, including a fibrosis or a fibrotic disease, such as renal fibrosis.

New imidazo[2,1-: B] thiazole-based aryl hydrazones: Unravelling their synthesis and antiproliferative and apoptosis-inducing potential

Babu, Bathini Nagendra,Devi, Ganthala Parimala,Kamal, Ahmed,Kumar, C. Ganesh,Rani Routhu, Sunitha,Shareef, Mohd Adil

supporting information, p. 1178 - 1184 (2020/11/03)

Herein, we have designed and synthesized new imidazo[2,1-b]thiazole-based aryl hydrazones (9a-w) and evaluated their anti-proliferative potential against a panel of human cancer cell lines. Among the synthesized compounds, 9i and 9m elicited promising cytotoxicity against the breast cancer cell line MDA-MB-231 with IC50 values of 1.65 and 1.12 μM, respectively. Cell cycle analysis revealed that 9i and 9m significantly arrest MDA-MB-231 cells in the G0/G1 phase. In addition, detailed biological studies such as annexin V-FITC/propidium iodide, DCFH-DA, JC-1 and DAPI staining assays revealed that 9i and 9m triggered apoptosis in MDA-MB-213 cells. Overall, the current work demonstrated the cytotoxicity and apoptosis-inducing potential of 9i and 9m in breast cancer cells and suggested that they could be explored as promising antiproliferative leads in the future. This journal is

Potent quinoline-containing combretastatin a-4 analogues: Design, synthesis, antiproliferative, and anti-tubulin activity

Ibrahim, Tarek S.,Hawwas, Mohamed M.,Malebari, Azizah M.,Taher, Ehab S.,Omar, Abdelsattar M.,O’boyle, Niamh M.,McLoughlin, Eavan,Abdel-Samii, Zakaria K.,Elshaier, Yaseen A. M. M.

, p. 1 - 22 (2020/11/19)

A novel series of quinoline derivatives of combretastatin A-4 incorporating rigid hydrazone and a cyclic oxadiazole linkers were synthesized and have demonstrated potent tubulin polymerization inhibitory properties. Many of these novel derivatives have shown significant antiproliferative activities in the submicromolar range. The most potent compound, 19h, demonstrated superior IC50 values ranging from 0.02 to 0.04 μM against four cancer cell lines while maintaining low cytotoxicity in MCF-10A non-cancer cells, thereby suggesting 19h’s selectivity towards proliferating cancer cells. In addition to tubulin polymerization inhibition, 19h caused cell cycle arrest in MCF-7 cells at the G2/M phase and induced apoptosis. Collectively, these findings indicate that 19h holds potential for further investigation as a potent chemotherapeutic agent targeting tubulin.

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