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2-Thiazolamine,4-(2,4-dichlorophenyl)-, commonly known as amiphenazole, is a white to off-white crystalline powder belonging to the thiazole class of chemical compounds. It serves as a versatile intermediate in the synthesis of pharmaceuticals and agrochemicals, primarily functioning as a building block for the development of various bioactive molecules. Amiphenazole has demonstrated antiproliferative and antifungal properties, making it a promising candidate for the treatment of cancer and infectious diseases. Furthermore, its activity as a histamine H1 receptor antagonist highlights its potential in the development of antihistamine medications.

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  • sodium 4-[[(2-chloro-1-oxoethyl)amino]methyl]-3-[4-[[4-(cyclohexylamino)-9,10-dioxo-1-anthracenyl]amino]phenoxy]-2-methylbenzenesulfonate

    Cas No: 93209-97-3

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  • 10 Milligram

  • Amadis Chemical Co., Ltd.
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  • 93209-97-3 Structure
  • Basic information

    1. Product Name: 2-Thiazolamine,4-(2,4-dichlorophenyl)-
    2. Synonyms: 2-Amino-4-(2,4-dichlorophenyl)thiazole;4-(2,4-Dichlorophenyl)thiazol-2-amine; [4-(2,4-Dichlorophenyl)thiazol-2-yl]amine
    3. CAS NO:93209-97-3
    4. Molecular Formula: C9H6Cl2N2S
    5. Molecular Weight: 245.1283
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 93209-97-3.mol
  • Chemical Properties

    1. Melting Point: 156-158°C
    2. Boiling Point: 396°Cat760mmHg
    3. Flash Point: 193.3°C
    4. Appearance: /
    5. Density: 1.498g/cm3
    6. Vapor Pressure: 1.76E-06mmHg at 25°C
    7. Refractive Index: 1.673
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: 2-Thiazolamine,4-(2,4-dichlorophenyl)-(CAS DataBase Reference)
    11. NIST Chemistry Reference: 2-Thiazolamine,4-(2,4-dichlorophenyl)-(93209-97-3)
    12. EPA Substance Registry System: 2-Thiazolamine,4-(2,4-dichlorophenyl)-(93209-97-3)
  • Safety Data

    1. Hazard Codes: Xi,T
    2. Statements: 25
    3. Safety Statements: 45
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 93209-97-3(Hazardous Substances Data)

93209-97-3 Usage

Uses

Used in Pharmaceutical Industry:
2-Thiazolamine,4-(2,4-dichlorophenyl)is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of bioactive molecules with potential therapeutic applications.
Used in Medicinal Chemistry Research:
Amiphenazole is utilized as a research compound in medicinal chemistry, where it aids in the exploration and understanding of its antiproliferative and antifungal properties, as well as its potential as a drug candidate for treating cancer and infectious diseases.
Used in Cancer Treatment:
2-Thiazolamine,4-(2,4-dichlorophenyl)is employed as a potential drug candidate in oncology, leveraging its antiproliferative properties to inhibit the growth and progression of cancer cells.
Used in Infectious Disease Treatment:
Amiphenazole is used as a potential therapeutic agent in the treatment of infectious diseases, capitalizing on its antifungal properties to combat fungal infections.
Used in Antihistamine Medication Development:
2-Thiazolamine,4-(2,4-dichlorophenyl)is utilized in the development of antihistamine medications due to its activity as a histamine H1 receptor antagonist, which can help alleviate symptoms associated with allergic reactions.

Check Digit Verification of cas no

The CAS Registry Mumber 93209-97-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,3,2,0 and 9 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 93209-97:
(7*9)+(6*3)+(5*2)+(4*0)+(3*9)+(2*9)+(1*7)=143
143 % 10 = 3
So 93209-97-3 is a valid CAS Registry Number.
InChI:InChI=1/C9H6Cl2N2S/c10-5-1-2-6(7(11)3-5)8-4-14-9(12)13-8/h1-4H,(H2,12,13)

93209-97-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-(2,4-DICHLOROPHENYL)-1,3-THIAZOL-2-AMINE

1.2 Other means of identification

Product number -
Other names 4-(2,4-dichlorophenyl)-1,3-thiazol-2-ylamine

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:93209-97-3 SDS

93209-97-3Relevant articles and documents

Solvent-free sonochemical kabachnic-fields reaction to synthesize some new α-aminophosphonates catalyzed by nano-BF3?SiO2

Ravikumar,Mohan,Subramanyam, Ch.,Rao, K. Prasada

, p. 400 - 407 (2018)

To obtain a rapid, efficient synthesis of some new α-aminophosphonates, ultrasonic irradiation has been applied to the reaction mixtures containing amine, aromatic or heteroaromatic aldehydes and triethyl phosphite. The Kabachnik-Fields reaction was performed by using nano-BF3?SiO2 as a recyclable catalyst under solvent free conditions. Key advantages of this procedure consist in the eco-friendly and highly efficient reaction conditions, high yields, an easy work-up procedure, short reaction times and solvent free conditions. All title compounds were characterized by spectral and elemental analysis. They were further screened for their in vitro antioxidant activity by the DPPH, O2? and NO methods. The majority of the title compounds showed good antioxidant activity when compared with the standard antioxidants.

COLLAGEN 1 TRANSLATION INHIBITORS AND METHODS OF USE THEREOF

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, (2021/12/31)

The present invention relates to novel collagen translation inhibitors 1, a composition, their preparation methods, and their uses for the treatment of fibrosis in particular, fibrosis of the lung, liver, kidney, cardiac and dermal fibrosis, IPF, wound he

Novel synthesis of 2-Aminothiazoles via Fe(III)-Iodine-catalyzed Hantzsch-type condensation

Ujwaldev, Sankuviruthiyil M.,Harry, Nissy Ann,Neetha, Mohan,Anilkumar, Gopinathan

supporting information, p. 646 - 653 (2020/10/20)

A novel iron-iodine catalyzed one pot synthesis of 2-aminothiazoles from methyl aryl ketones and thiourea is demonstrated. This protocol can be considered as a catalyzed version of the classical Hantzsch aminothiazole synthesis as it enables the in situ generation of α-iodoketones in the reaction medium using catalytic amount of iodine leading to Hantzsch condensation with thiourea. The supply of iodine for multiple catalytic cycles is ensured by using catalytic amounts of iron as it enables iodide to iodine oxidation. The generality of this protocol is also well established in this manuscript by synthesizing a variety of 2-aminothiazoles from different ketones and thiourea.

Design, synthesis and molecular modelling studies of 1-methyl-3-(4-substituted phenyl-1,3thiazol-2-yl)-2-(pyridin-3-yl)-2,3-dihydroquinazolin-4(1h)-ones as potent anticancer agents

Nagaladinne, Nizamuddin,Hindustan, Abdul Ahad,Nayakanti, Devanna

, p. 3067 - 3074 (2021/01/06)

The present study involves the design, synthesis, characterization and molecular docking studies of biologically active quinazolin-4-ones, which were synthesized by condensing 2-amino-4-substituted phenylthiazole with N-methylbenzoxazin-4-one. The N-methylbenzoxazin-4-one and 2-amino-4-substituted phenylthiazole were synthesized from N-methylanthranilic acid and substituted ketones, respectively. The ADME properties determined the synthetic accessibility of quinazolin-4-ones by in silico Swiss ADME. The colorectal anticancer screening was done by using cell HT-29 human colorectal adenocarcinoma based on molecular docking studies on 3GC7-the structure of p38alpha in complex with dihydroquinazolinone. Finally, compounds 5Dh8, 5DF6, 5Db2 and 5Di9 exhibited better activity at a concentration 10 μg/mL when compared to 5-fluorouracil. The ADME properties revealed that all the compounds were within the range and docking studies showed the highest binding with glide score -7.19 and -7.027 Kcal/mol compared to the target protein -10.67 Kcal/mol.

Design, synthesis, and biological evaluation of novel arylcarboxamide derivatives as anti-tubercular agents

Alsayed, Shahinda S. R.,Beh, Chau Chun,Bishai, William R.,Foster, Neil,Gunosewoyo, Hendra,Lun, Shichun,Luna, Giuseppe,Payne, Alan D.

, p. 7523 - 7540 (2020/03/13)

Our group has previously reported several indolecarboxamides exhibiting potent antitubercular activity. Herein, we rationally designed several arylcarboxamides based on our previously reported homology model and the recently published crystal structure of the mycobacterial membrane protein large 3 (MmpL3). Many analogues showed considerable anti-TB activity against drug-sensitive (DS) Mycobacterium tuberculosis (M. tb) strain. Naphthamide derivatives 13c and 13d were the most active compounds in our study (MIC: 6.55, 7.11 μM, respectively), showing comparable potency to the first line anti-tuberculosis (anti-TB) drug ethambutol (MIC: 4.89 μM). In addition to the naphthamide derivatives, we also identified the quinolone-2-carboxamides and 4-arylthiazole-2-carboxamides as potential MmpL3 inhibitors in which compounds 8i and 18b had MIC values of 9.97 and 9.82 μM, respectively. All four compounds retained their high activity against multidrug-resistant (MDR) and extensively drug-resistant (XDR) M. tb strains. It is worth noting that the two most active compounds 13c and 13d also exhibited the highest selective activity towards DS, MDR and XDR M. tb strains over mammalian cells [IC50 (Vero cells) ≥ 227 μM], indicating their potential lack of cytotoxicity. The four compounds were docked into the MmpL3 active site and were studied for their drug-likeness using Lipinski's rule of five.

Synthesis and Molecular Docking Studies of Some 1,2-Dimethyl-3(4-substituted phenyl-1,3-thiazol-2-yl)2,3-dihydroquinazolin-4(1H)-ones as Anticancer Agents

Nizamuddin,Ahad, Hindustan Abdul,Devanna, Nayakanti

, p. 571 - 579 (2021/02/02)

Synthesis of 1, 2-dimethyl-3(4-substituted phenyl-1,3-thiazol-2-yl)2,3-dihydro quinazolin-4(1H)-ones (5Aa1-5Ak11) derivatives was effected by refluxing 1,2-dimethylbenzoxazine-4-one with different 4-substituted phenyl-1,3-thiazol-2-amines. Synthesized compounds were characterized through elemental analysis, infrared, proton nuclear magnetic resonance, and Carbon-13 nuclear magnetic resonance. Molecular docking studies were carried out using Schr?dinger Glide (version 2020_1) which was docked into selective P38alpha and Activin A Receptor Type 1 (ACVR1) Activin receptor-like kinase-2 (ALK2) kinase with Protein Data Bank (PDB) code 3GC7, 6GI6. Based on the docking score of synthesized quinazolin-4-one derivatives, co-crystallized ligands interaction was evaluated with 5-fluorouracil (5-FU) as a reference drug. Compounds 5Ae5, 5Aa1, 5Ai9, and 5Ab2 with P38alpha, 5Af6, 5Ae5, 5Ad4, and 5Ab2 with ACVR1 (ALK2) kinase score were -7.265, -7.078, -7.058, and -6.836; -8.929, -8.749, -8.735, and -8.464 Kcal/mol against enzymes responsible for cancer treatment. The results indicated that quinazolin-4-one derivatives had scored better than ligand and 5-FU.

SUBSTITUTED PROPANAMIDES AS INHIBITORS OF NUCLEASES

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Page/Page column 11; 13; 23; 24; 38, (2019/11/12)

The invention provides compounds represented by the structural formula (1): wherein R1, R2, R3, R4, R5, R6 are as defined in the claims. The compounds are inhibitors of nucleases, and are useful in particular in a method of treatment and/or prevention of proliferative diseases, neurodegenerative diseases, and other genomic instability associated diseases.

Citric Acid-catalyzed Synthesis of 2,4-Disubstituted Thiazoles from Ketones via C–Br, C–S, and C–N Bond Formations in One Pot: A Green Approach

Gundala, Trivikram Reddy,Godugu, Kumar,Nallagondu, Chinna Gangi Reddy

, p. 1408 - 1416 (2017/10/23)

An improved and greener protocol has been developed for the synthesis of 2,4-disubstituted thiazoles via C–Br, C–S, and, C–N bond formations in a single step from readily available ketones, N-bromosuccinimide (NBS), and thiourea catalyzed by citric acid in a mixture of ethanol and water (3:1) under reflux conditions. This method has the advantages of freedom from the isolation of lachrymatory α-bromoketones, ease of carrying out, cleaner reaction profile, broad substrate scope, freedom from chromatographic purification, and suitability for large-scale synthesis.

Microwave-assisted synthesis of novel N-(4-phenylthiazol-2-yl)-benzo[d]thiazole-, thiazolo[4,5-b]pyridine-, thiazolo[5,4-b]pyridine- and benzo[d]oxazole-2-carboximidamides inspired by marine topsentines and nortopsentines

Deau, Emmanuel,Dubouilh-Benard, Carole,Levacher, Vincent,Besson, Thierry

, p. 5532 - 5540 (2015/03/30)

We report the synthesis of novel N-(4-phenylthiazol-2-yl)-substituted benzo[d]thiazole-, thiazolo[4,5-b]pyridine-, thiazolo[5,4-b]pyridine- and benzo[d]oxazole-2-carboximidamides, which were inspired by marine topsentines and nortopsentines. Condensation of 4,5-dichloro-1,2,3-dithiazolium chloride (Appel salt) with various ortho-halogenated anilines, aminopyridines and aminophenols gave the corresponding aryliminodithiazoles in good to excellent yields. Copper(I)-mediated or nucleophilic-assisted cyclization of aryliminodithiazoles furnished cyano-functionalized benzo[d]thiazoles, thiazolo[4,5-b]- and thiazolo[5,4-b]-pyridines and benzo[d]oxazoles. The latter were condensed with substituted 4-phenylthiazol-2-amines to furnish twenty seven new polyaromatic carboximidamides in moderate to good yields.

Discovery of novel N-(5-(arylcarbonyl)thiazol-2-yl)amides and N-(5-(arylcarbonyl)thiophen-2-yl)amides as potent RORγt inhibitors

Wang, Yonghui,Cai, Wei,Zhang, Guifeng,Yang, Ting,Liu, Qian,Cheng, Yaobang,Zhou, Ling,Ma, Yingli,Cheng, Ziqiang,Lu, Sijie,Zhao, Yong-Gang,Zhang, Wei,Xiang, Zhijun,Wang, Shuai,Yang, Liuqing,Wu, Qianqian,Orband-Miller, Lisa A.,Xu, Yan,Zhang, Jing,Gao, Ruina,Huxdorf, Melanie,Xiang, Jia-Ning,Zhong, Zhong,Elliott, John D.,Leung, Stewart,Lin, Xichen

supporting information, p. 692 - 702 (2014/01/23)

Novel series of N-(5-(arylcarbonyl)thiazol-2-yl)amides and N-(5-(arylcarbonyl)thiophen-2-yl)amides were discovered as potent retinoic acid receptor-related orphan receptor-gamma-t (RORγt) inhibitors. SAR studies of the RORγt HTS hit 6a led to identification of thiazole ketone amide 8h and thiophene ketone amide 9g with high binding affinity and inhibitory activity of Th17 cell differentiation. Compound 8h showed in vivo efficacy in both mouse experimental autoimmune encephalomyelitis (EAE) and collagen induced arthritis (CIA) models via oral administration.

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