347-81-9

Usage

Uses

Used in Organic Synthesis:
N-(4-Fluorophenyl)-4-nitrobenzaMide, 97% is used as a building block in organic synthesis for the creation of various biologically active compounds. Its unique structure and functional groups allow for versatile chemical reactions, enabling the synthesis of a wide range of organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, N-(4-Fluorophenyl)-4-nitrobenzaMide, 97% is used as a key intermediate in the development of new drugs. Its presence in the molecular structure can impart specific biological activities, making it a valuable component in the design and synthesis of potential therapeutic agents.
Used in Chemical Research:
N-(4-Fluorophenyl)-4-nitrobenzaMide, 97% is also utilized in chemical research to study the properties and reactivity of its functional groups. Understanding its behavior in various chemical reactions can provide insights into the development of new synthetic methods and the discovery of novel compounds with potential applications in various fields.

InChI:InChI=1/C13H9FN2O3/c14-10-3-5-11(6-4-10)15-13(17)9-1-7-12(8-2-9)16(18)19/h1-8H,(H,15,17)

Upstream product

• 122-04-3 4-nitro-benzoyl chloride 
• 371-40-4 4-fluoroaniline 
• 62-23-7 4-nitro-benzoic acid 
• 3460-11-5 4-nitrobenzanilide 

Downstream Products

• 1393816-17-5 C₂₁H₁₄F₂N₂OS 
• 1393815-45-6 6-fluoro-2-(4-(5-(4-fluoro-3-methoxyphenyl)-1H-imidazol-1-yl)phenyl)benzo[d]thiazole 
• 1458715-45-1 6-fluoro-2-(4-(2-methyl-5-p-tolyl-1H-pyrrol-1-yl)phenyl)benzo[d]thiazole 
• 1458715-46-2 6-fluoro-2-(4-(2-(4-fluorophenyl)-5-methyl-1H-pyrrol-1-yl)phenyl)benzo[d]thiazole 
• 1458715-47-3 6-fluoro-2-(4-(2-(4-methoxyphenyl)-5-methyl-1H-pyrrol-1-yl)phenyl)benzo[d]thiazole 
• 1458715-48-4 6-fluoro-2-(4-(2-methyl-5-(4-nitrophenyl)-1H-pyrrol-1-yl)phenyl)benzo[d]thiazole 
• 1458715-49-5 6-fluoro-2-(4-(2-methyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrrol-1-yl)phenyl)benzo[d]thiazole 
• 167565-72-2 N-(4-fluorophenyl)-4-nitro-1-benzenecarbothioamide 
• 698988-07-7 4-amino-N-(4-fluorophenyl)benzamide 
• 328087-23-6 2-(4-amino-3-iodophenyl)-6-fluorobenzothiazole 
• 343975-46-2 6-fluoro-2-(4-nitrophenyl)benzo[d]thiazole 

Relevant academic research and scientific papers

Novel series of benzo[d]thiazolyl substituted-2-quinolone hybrids: Design, synthesis, biological evaluation and in-silico insights

A novel series of 3-(2-(4-(substituted-benzo[d]thiazol-2-yl)phenylamino)acetyl)-4?hydroxy-1-methyl/phenyl quinolin-2(1H)-one (7a-f and 8a-f) were synthesized. Reaction of appropriately substituted-2-(4-amino phenyl)benzo[d]thiazole (4a-f) with 3-(2-bromoacetyl)-4?hydroxy-1-methyl/phenyl quinolin-2(1H)-one (5/6) in the presence of glacial acetic acid resulted in desired compounds. Structures of the synthesized compounds were characterized based on their spectral (IR, 1H NMR, 13C NMR and MS) and elemental analysis. The cytotoxicity screening studies revealed that MCF-7 and WRL68 cancer cells were sensitive to all the tested compounds. Out of twelve novel hybrids, compound 8f displayed the most significant anticancer activity. Docking studies were performed in order to understand the binding mode of the title compounds at the active site of the target enzyme (EGFR tyrosine kinase, 1M17). Compounds 8f and 7f displayed prominent and conserved binding interactions against 1M17. In addition, compounds 7e, 7f, 8e, and 8f exhibited interesting in vitro antibacterial activity, especially against Gram-negative bacteria E. coli. In summary, the novel benzo[d]thiazolyl substituted-2-quinolone hybrid (8f) could be considered as promising hit and could be further exploited for developing potential anticancer/antimicrobial agents.

Applicability of aluminum amalgam to the reduction of arylnitro groups

An array of arylnitro compounds with various functionality were treated with freshly-prepared aluminum amalgam in THF/water solution and resulted in the corresponding arylamines. The Al(Hg)-mediated reductions are relatively rapid with consumption of the amalgam and disappearance of starting material occurring over 20–30 min. The workup of the reductions involves only removal of the insoluble by-products by filtration followed by concentration. Only in some cases is chromatography required to secure the pure product. The desired arylamines are furnished in quantities of 25–100 mg, which in some cases, could be taken on to the next reaction without further purification. Reductions of 4-nitrobenzyl derivatives of carbohydrates or nucleosides were selective in affording the corresponding 4-aminobenzyl products. To show applicability in click chemistry, selected aminobenzyl products are directly azidated to yield products that were then used in click reactions to afford the corresponding 1,2,3-triazoles.

Design, synthesis and biological evaluation of novel 2-phenyl pyrimidine derivatives as potent Bruton's tyrosine kinase (BTK) inhibitors

BTK is an effective target for the treatment of B-cell malignant tumors and autoimmune diseases. In this work, a series of 2-phenyl pyrimidine derivatives were prepared and their preliminary in vitro activities on B-cell leukemia cells as well as the BTK enzyme were determined. The results showed that compound 11g displayed the best inhibitory activity on BTK with an inhibition rate of 82.76% at 100 nM and excellent anti-proliferation activity on three B-cell leukemia lines (IC50 = 3.66 μM, 6.98 μM, and 5.39 μM against HL60, Raji and Ramos, respectively). Besides, the flow cytometry analysis results indicated that 11g inhibited the proliferation of the Raji cells in a dose- and time-dependent manner, and blocked the Ramos cells at the G0/G1 phase, which is in accordance with the positive control ibrutinib. The mechanism investigation demonstrated that 11g could inhibit the phosphorylation of BTK and its downstream substrate phospholipase γ2 (PLCγ2). All these results showed that 11g was a promising lead compound that merited further optimization as a novel class of BTK inhibitor for the treatment of B-cell lymphoblastic leukemia.

Identification of new pyrrolo[2,3-d]pyrimidines as potent VEGFR-2 tyrosine kinase inhibitors: Design, synthesis, biological evaluation and molecular modeling

Vascular endothelial growth factor receptor-2 (VEGFR-2) plays a crucial role in cancer angiogenesis. In the current study, a series of novel pyrrolo[2,3-d]pyrimidine based-compounds was designed and synthesized as VEGFR-2 inhibitors, in accordance to the structure activity relationship (SAR) studies of known type II VEGFR-2 inhibitors. The newly synthesized compounds were evaluated for their ability to inhibit VEGFR-2 kinase enzyme in vitro. All the tested compounds demonstrated highly potent dose-related VEGFR-2 inhibition with IC50 values in nanomolar range. Among these compounds, pyrrolo[2,3-d]pyrimidine derivatives carrying biaryl urea moieties (12d and 15c) exhibited IC50 values of 11.9 and 13.6 nM respectively. Additionally, most of the newly synthesized final compounds were tested on 60 human cancer cell lines. Docking of these compounds into the inactive conformation of VEGFR-2 was performed which showed comparable binding modes to that of the FDA approved VEGFR-2 kinase inhibitors. These newly discovered potent kinase inhibitors could be considered as potential candidates for the development of new targeted anticancer agent.

Synthesis and biological evaluation of cis-restricted triazole/tetrazole mimics of combretastatin-benzothiazole hybrids as tubulin polymerization inhibitors and apoptosis inducers

A series of colchicine site binding tubulin inhibitors were synthesized by the modification of the combretastatin pharmacophore. The ring B was replaced by the pharmacologically relevant benzothiazole scaffolds, and the cis configuration of the olefinic b

Design, synthesis and structure-activity relationship of new HSL inhibitors guided by pharmacophore models

Hormone-sensitive lipase (HSL) is a critical enzyme involved in the hormonally regulated release of fatty acids and glycerol from adipocyte lipid stores. Its inhibition may improve insulin sensitivity and blood glucose handling in type 2 diabetes. Accordingly, many small-molecule HSL inhibitors have recently been identified. In continuation of our efforts for discovery of new HSL inhibitors, we prepared a variety of esters, amides, sulfonamides and sulfonate esters capable of fitting two pharmacophore models that we developed and published earlier. The tested compounds were synthesized via coupling reactions of aroyl chlorides or sulfonyl chlorides with phenols, amines and related derivatives. Our efforts led to the identification of interesting compounds of low micromolar anti-HSL bioactivities, which have potential to be developed into effective antidiabetic agents.

Hypervalent iodine mediated para -selective fluorination of anilides

A metal-free method for the direct regioselective fluorination of anilides has been developed. In the presence of bis(tert-butylcarbonyloxy)iodobenzene (PhI(OPiv)2) and hydrogen fluoride-pyridine, the para-fluorination products of anilides were obtained in moderate to good yields. Because of its operational safety and the use of readily available reagents, this new procedure provides facile access to a variety of para-fluorinated anilides.

Synthesis and study of benzothiazole conjugates in the control of cell proliferation by modulating Ras/MEK/ERK-dependent pathway in MCF-7 cells

By applying a methodology, a series of benzothiazole-pyrrole based conjugates (4a-r) were synthesized and evaluated for their antiproliferative activity. Compounds such as 4a, 4c, 4e, 4g-j, 4m, 4n, 4o and 4r exhibited significant cytotoxic effect in the MCF-7 cell line. Cell cycle effects were examined for these conjugates at 2 μM as well as 4 μM concentrations and FACS analysis show an increase of G2/M phase cells with concomitant decrease of G1 phase cells thereby indicating G2/M cell cycle arrest by them. Interestingly 4o and 4r are effective in causing apoptosis in MCF-7 cells. Moreover, 4o showed down regulation of oncogenic expression of Ras and its downstream effector molecules such as MEK1, ERK1/2, p38 MAPK and VEGF. The apoptotic aspect of this conjugate is further evidenced by increased expression of caspase-9 in MCF-7 cells. Hence these small molecules have the potential to control both the cell proliferation as well as the invasion process in the highly malignant breast cancers.

2-PHENYL BENZOTHIAZOLE LINKED IMIDAZOLE COMPOUNDS AS POTENTIAL ANTICANCER AGENTS AND PROCESS FOR THE PREPARATION THEREOF

The present invention provides 2-phenyl benzothiazole linked imidazole compounds of formula A as anti cancer agent against fifty three human cancer cell lines. (General formula A) wherein (II) R=H or OCH3; R1=H, F or OCH3; R2=H or OCH3; R3=H, NH2, F or OCH3; R4=H, NH2 or OCH3; R5=H, NH2, F, CF3 or OCH3; R6=H or OCH3; R7=H or OCH3; R8=H or OCH3.

An efficient one-pot synthesis of benzothiazolo-4β-anilino- podophyllotoxin congeners: DNA topoisomerase-II inhibition and anticancer activity

An efficient one-pot iodination methodology for the synthesis of benzothiazolo-4β-anilino-podophyllotoxin (5a-h) and benzothiazolo-4β- anilino-4-O-demethylepipodophyllotoxin (6a-h) congeners has been successfully developed by using zirconium tetrachloride