Tag: 200-300

Design, synthesis and evaluation of novel (S)-tryptamine derivatives containing an allyl group and an aryl sulfonamide unit as anticancer agents was written by Guo, Zhenbo;Xu, Yiming;Peng, Yujie;Haroon ur Rashid;Quan, Wei;Xie, Peng;Wu, Lichuan;Jiang, Jun;Wang, Lisheng;Liu, Xu. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2019.Synthetic Route of C7H4ClF3O2S This article mentions the following:

A series of (S)-tryptamine derivatives containing an allyl group and an aryl sulfonamide unit, I (R = Ph, 3-Cl-4-FC₆H₃, 4-Br-2-ClC₆H₄, etc.) and II [R = Ph, 2,4,6-(Me₂CH)₃C₆H₂], were designed, synthesized and evaluated for their potential application as anticancer agents. The structures of the synthesized compounds were characterized by ¹H NMR, ¹³C NMR and ESI-MS spectral analyses. The target compounds were evaluated for their in vitro cytotoxicity against HepG2, HeLa, CNE1 and A549 human cancer cell lines. Some of the synthesized compounds showed moderate to good anticancer activities against four selected cancer cell lines, among of which I [R = 2,4,6-(Me₂CH)C₆H₂] (III) was found to be the most active analog possessing IC₅₀ values 16.5-18.7 μM. Further mechanism studies revealed that compound III could significantly induce HepG2 cell cycle arrest at G1 phase, promote cell apoptosis, and inhibit the colony formation as well. In the experiment, the researchers used many compounds, for example, 3-(Trifluoromethyl)benzene-1-sulfonyl chloride (cas: 777-44-6Synthetic Route of C7H4ClF3O2S).

3-(Trifluoromethyl)benzene-1-sulfonyl chloride (cas: 777-44-6) belongs to organic chlorides. An organic chloride is an organic compound containing at least one covalently bonded atom of chlorine. Their wide structural variety and divergent chemical properties lead to a broad range of names and applications. The haloform reaction, using chlorine and sodium hydroxide, is also able to generate alkyl halides from methyl ketones, and related compounds. Chloroform was formerly produced thus.Synthetic Route of C7H4ClF3O2S

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthesis and tyrosinase inhibitory properties of novel isoquinoline urea/thiourea derivatives was written by Genc, Hayriye;Zengin, Mustafa;Yavuz, Emre;Gencer, Nahit;Arslan, Oktay. And the article was included in Artificial Cells, Nanomedicine, and Biotechnology in 2014.Synthetic Route of C7H3Cl2NS This article mentions the following:

A new series of isoquinoline urea/thiourea derivatives I (X = O, S; R = Ph, n-Bu, i-Pr, n-Pr, n-Hexyl, etc.) were synthesized, and their inhibitory effects on tyrosinase were evaluated. Isoquinoline urea/thiourea derivatives were obtained as a result of the reaction of 5-aminoisoquinoline with isocyanates or isothiocyanates. The result showed that all the synthesized compounds inhibited the tyrosinase enzyme activity. Among the compounds synthesized, 1-(4-chlorophenyl)-3-(isoquinolin-5-yl)thiourea was found to be the most active one (Ki = 119.22 μM), and the inhibition kinetics analyzed using Lineweaver-Burk double reciprocal plots revealed that compound I (X= S; R = 4-ClPh) was a competitive inhibitor. HOMO-LUMO energy levels for selected synthesized compounds were calculated using Gaussian software. In the experiment, the researchers used many compounds, for example, 2,4-Dichlorophenylisothiocyanate (cas: 6590-96-1Synthetic Route of C7H3Cl2NS).

2,4-Dichlorophenylisothiocyanate (cas: 6590-96-1) belongs to organic chlorides. Organochlorines are organic compounds having multiple chlorine atoms. They were the first synthetic pesticides that were used in agriculture. They are resistant to most microbial and chemical degradations. Organochlorine compounds are lipophylic, meaning they are more soluble in fat than in water. This gives them a high tenancy to accumulate in the food chain (biomagnification).Synthetic Route of C7H3Cl2NS

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Discovery of a Potent and Selective ATAD2 Bromodomain Inhibitor with Antiproliferative Activity in Breast Cancer Models was written by Winter-Holt, Jon J.;Bardelle, Catherine;Chiarparin, Elisabetta;Dale, Ian L.;Davey, Paul R. J.;Davies, Nichola L.;Denz, Christopher;Fillery, Shaun M.;Guerot, Carine M.;Han, Fujin;Hughes, Samantha J.;Kulkarni, Meghana;Liu, Zhaoqun;Milbradt, Alexander;Moss, Thomas A.;Niu, Huijun;Patel, Joe;Rabow, Alfred A.;Schimpl, Marianne;Shi, Junjie;Sun, Dongqing;Yang, Dejian;Guichard, Sylvie. And the article was included in Journal of Medicinal Chemistry in 2022.Synthetic Route of C7H5ClN2O4 This article mentions the following:

ATAD2 is an epigenetic bromodomain-containing target which is overexpressed in many cancers and has been suggested as a potential oncol. target. While several small mol. inhibitors have been described in the literature, their cellular activity has proved to be underwhelming. In this work, we describe the identification of a novel series of ATAD2 inhibitors by high throughput screening, confirmation of the bromodomain region as the site of action, and the optimization campaign undertaken to improve the potency, selectivity, and permeability of the initial hit. The result is compound 5 (AZ13824374)(I), a highly potent and selective ATAD2 inhibitor which shows cellular target engagement and antiproliferative activity in a range of breast cancer models. In the experiment, the researchers used many compounds, for example, Methyl 6-chloro-5-nitronicotinate (cas: 59237-53-5Synthetic Route of C7H5ClN2O4).

Methyl 6-chloro-5-nitronicotinate (cas: 59237-53-5) belongs to organic chlorides. Organic chlorides can cause corrosion in pipelines, valves and condensers, and cause catalyst poisoning. The hydrocarbon processing industry (HPI) and others are affected by damage caused by these substances. Alkyl chlorides readily react with amines to give substituted amines. Alkyl chlorides are substituted by softer halides such as the iodide in the Finkelstein reaction.Synthetic Route of C7H5ClN2O4

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Chemoselective N-tert-butyloxycarbonylation of amines in glycerol was written by Ingale, Ajit P.;More, Vishal K.;Gangarde, Uddhav S.;Shinde, Sandeep V.. And the article was included in New Journal of Chemistry in 2018.Formula: C11H14ClNO2 This article mentions the following:

A catalyst-free, efficient and green protocol has been developed for the chemoselective N-Boc protection of amines by using glycerol as a solvent at room temperature A variety of functionalized amines, such as aliphatic, aromatic as well as heteroaromatic were protected using the developed protocol. N-tert-butyloxycarbonylated derivatives were formed without the formation of isocyanate, urea, N,N-di-t-Boc, or oxazolidinone as side products. The operational simplicity, cleaner reaction, rapid reaction convergence, functional group tolerance, excellent yield, high selectivity, catalyst-free feature and solvent recyclability are the distinct advantages of this protocol. Owing to these merits, this protocol is feasible, economical and environmentally benign. In the experiment, the researchers used many compounds, for example, tert-Butyl (4-chlorophenyl)carbamate (cas: 18437-66-6Formula: C11H14ClNO2).

tert-Butyl (4-chlorophenyl)carbamate (cas: 18437-66-6) belongs to organic chlorides. Organochlorines are organic compounds having multiple chlorine atoms. They were the first synthetic pesticides that were used in agriculture. They are resistant to most microbial and chemical degradations. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst.Formula: C11H14ClNO2

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Studies on structures and pKa values of benzoic acid derivatives was written by Qi, Yu-hua;Xu, Lu;Zhang, Qing-you. And the article was included in Jisuanji Yu Yingyong Huaxue in 2002.Category: chlorides-buliding-blocks This article mentions the following:

The topol. indexes were used in the QSPR studies of the structures of benzoic acid derivatives and their pK_a values. The orthogonal method is performed for selection of the variables. Satisfactory results were achieved. In the experiment, the researchers used many compounds, for example, 2-Chloro-6-nitrobenzoic acid (cas: 5344-49-0Category: chlorides-buliding-blocks).

2-Chloro-6-nitrobenzoic acid (cas: 5344-49-0) belongs to organic chlorides. Organic chlorides can cause corrosion in pipelines, valves and condensers, and cause catalyst poisoning. The hydrocarbon processing industry (HPI) and others are affected by damage caused by these substances. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst.Category: chlorides-buliding-blocks

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Mechanistic investigation of oxidation of metronidazole with N-chlorosaccharin in acid medium: a kinetic approach was written by Singh, Santosh Kumar;Khan, M. U.;Dwivedi, H. P.;Chauhan, D. B. S.;Gupta, H. D.. And the article was included in International Journal of Green and Herbal Chemistry in 2013.Safety of 2-Chlorobenzo[d]isothiazol-3(2H)-one 1,1-dioxide This article mentions the following:

A kinetic study of oxidation of Mitronidazole (MTZ) is an anti-bacterial and anti-protozoal drug, with N-chlorosaccharin (NCSA) has been carried out in presence of HClO₄ in aqueous acetic acid medium at 308 K. The reaction is fully HClO₄ acid catalyzed and retardation was observed when saccharin was added in reaction mixture Variation of ionic strength of the medium shows negligible effect on rate of reaction. Increase in dielec. permittivity of the medium increases the rate of oxidation The stoichiometry of the reaction was found to be 1:1. The reported oxidation product of MTZ was identified as the 2-methyl-5-nitro imidazole-N¹-acetaldehyde which was detected by conventional methods and spot test. Various activation parameters have been evaluated. The reaction constants involved in the proposed mechanisms were computed. The proposed mechanisms were in good consistent with the observed exptl. results. In the experiment, the researchers used many compounds, for example, 2-Chlorobenzo[d]isothiazol-3(2H)-one 1,1-dioxide (cas: 14070-51-0Safety of 2-Chlorobenzo[d]isothiazol-3(2H)-one 1,1-dioxide).

2-Chlorobenzo[d]isothiazol-3(2H)-one 1,1-dioxide (cas: 14070-51-0) belongs to organic chlorides. Chlorinated organic compounds are found in nearly every class of biomolecules and natural products including alkaloids, terpenes, amino acids, flavonoids, steroids, and fatty acids. Organochlorine compounds are lipophylic, meaning they are more soluble in fat than in water. This gives them a high tenancy to accumulate in the food chain (biomagnification).Safety of 2-Chlorobenzo[d]isothiazol-3(2H)-one 1,1-dioxide

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Structure-Based Design of Potent and Ligand-Efficient Inhibitors of CTX-M Class A β-Lactamase was written by Nichols, Derek A.;Jaishankar, Priyadarshini;Larson, Wayne;Smith, Emmanuel;Liu, Guoqing;Beyrouthy, Racha;Bonnet, Richard;Renslo, Adam R.;Chen, Yu. And the article was included in Journal of Medicinal Chemistry in 2012.Quality Control of 2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid This article mentions the following:

The emergence of CTX-M class A extended-spectrum β-lactamases poses a serious health threat to the public. We have applied structure-based design to improve the potency of a novel noncovalent tetrazole-containing CTX-M inhibitor (K_i = 21 μM) more than 200-fold via structural modifications targeting two binding hot spots, a hydrophobic shelf formed by Pro167 and a polar site anchored by Asp240. Functional groups contacting each binding hot spot independently in initial designs were later combined to produce analogs with submicromolar potencies, including 6-trifluoromethyl-3H-benzoimidazole-4-carboxylic acid [3-(1H-tetrazol-5-yl)-phenyl]-amide, which had a K_i value of 89 nM and reduced the MIC of cefotaxime by 64-fold in CTX-M-9 expressing Escherichia coli. The in vitro potency gains were accompanied by improvements in ligand efficiency (from 0.30 to 0.39) and LipE (from 1.37 to 3.86). These new analogs represent the first nM-affinity noncovalent inhibitors of a class A β-lactamase. Their complex crystal structures provide valuable information about ligand binding for future inhibitor design. In the experiment, the researchers used many compounds, for example, 2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid (cas: 22227-59-4Quality Control of 2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid).

2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid (cas: 22227-59-4) belongs to organic chlorides. Organic chlorides are compounds containing a carbon-chlorine bond, which are widely used in the oil field as a wax dissolver. While alkyl bromides and iodides are more reactive, alkyl chlorides tend to be less expensive and more readily available. Alkyl chlorides readily undergo attack by nucleophiles.Quality Control of 2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Polar effects of substituents on the reaction rates of 4-R and 5-R-2-nitrochlorobenzenes with pipefidine in benzene was written by Greizerstein, W.;Bonelli, R. A.;Brieux, J. A.. And the article was included in Journal of the American Chemical Society in 1962.Related Products of 16588-16-2 This article mentions the following:

The rate constants for the reaction of fourteen 4-Rand of twelve 6-R-2-nitrochlorobenzenes with piperidine in benzene solution were determined The reactions were carried out at constant temperature in sealed tubes each containing 10 ml. benzene solution of the reactants, 0.1M in the halogen compound and 1.0M in piperidine. Cl^– was determined by potentiometric titration after addition of 10 ml. 20% HNO₃. Rate constants were calculated by means of the equation k₂ = {2.303/[t(b – 2a)]} log {a(b – 2x)/b(a – x)}, where a and b were the molar concentrations of the halogen compound and piperidine, rasp., and x the concentration of Cl^– at time t. Data from duplicate runs did not differ by more than 1% and rate constants were reproducible within ±2% by independent experiments A spectrophotometric technique was used for compounds having the substituents: 4-NO₂, 3-CN, 4-CO₂Et, 4-PhN:N, 4-F₃C, and 5-CN. The absorption due to the substituted N-phenylpiperidine produced in the reaction was measured at 390420 mμ with a Beckman DU spectrophotometer. Initial concentrations ranged from 10^-4 to 10^-5M for the halogen compound and piperidine was 10²-10³ times in excess. Samples were removed from the thermostat, cooled rapidly to room temperature, and the absorbency measured directly. Pseudomonomol. rate constants were calculated graphically from the plot of O.D._∞exptl.-O.D._t; versus t (O.D, = optical d.); second-order rate constants were obtained from these by dividing by the concentration of piperidine. The results were tabulated and showed that in the nucleophilic substitution of these compounds the polarity of the substituted carbon atom was mainly determined by the overall polar effect of the substituent. The reaction followed the Hammett relationship log k_R/k_H = σ^*ρ. Using Jaffe’s σ^* values, which are equivalent to Hammett’s σ-constants for most substituents studied, a ρ-value of +3.80 with a correlation coefficient r = 0.934 resulted. For the 4-R-2-nitrochlorobenzenes, alone a ρ-constant of +4.08 with a correlation coefficient of 0.922 was obtained. In order to estimate the mesomeric interaction between a 5-substituent R and the nitro group para to each other, the values of log k_2-5R versus σ^*_meta were introduced into Hammett’s graphic plot of log k_2-4R versus σ^*_4R with ρ = 4.08. From this, the difference between σ^*_meta values employed and the amended σ-values fitting the exptl. data into the equation log k_2-5R = log k_2-H + 4.08. σ_amended was evaluated for each m-substituent. The differences for most substituents were small, but for m-CN, m-CO₂Et, and m-Ph the σ_amended values were smaller than the σ-constants by 0.24, 0.20, and 0.20 units, resp., showing that the activating influence of the nitro group ortho to the site of reaction was roughly constant but smaller than the overall effect in most compounds studied. 4-Chloro-3-nitrobenzotrifluoride and 4-chloro-3-nitroazobenzene showed an inversion of relative reactivity between 35 and 45°, but the order for the more reactive compounds at 45°, k_4-No2 > k_4-CN > k_4-CO2Et > k_4-F3C gt; k_4-C6H5N2 > k_4-CO2H gt; k_4-halogen was that expected from their total polar effects upon the site of substitution. The 3-chloro-4-nitrobenzoic acid reacted slower than the p- and o-substituted isomer. The substituents 4-OMe, 4-OEt, and 4-NH₂ were found to be deactivating by their mesomeric effect, while halogens produced a marked increase in the rate, specially from the m-position, due to their neg. inductive effect. A Me group in the m-position gave a slight decrease of the rate, this being more pronounced if Me was in the p-position. The phenyl group slightly enhanced the reactivity from the m-positions, a greater increment being observed from the p-position. In the experiment, the researchers used many compounds, for example, Ethyl 4-chloro-3-nitrobenzoate (cas: 16588-16-2Related Products of 16588-16-2).

Ethyl 4-chloro-3-nitrobenzoate (cas: 16588-16-2) belongs to organic chlorides. Organic chlorides can be used in production of: PVC, pesticides, chloromethane, teflon, insulators. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst.Related Products of 16588-16-2

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Design and Optimization of an Acyclic Amine Series of TRPV4 Antagonists by Electronic Modulation of Hydrogen Bond Interactions was written by Patterson, Jaclyn R.;Terrell, Lamont R.;Donatelli, Carla A.;Holt, Dennis A.;Jolivette, Larry J.;Rivero, Ralph A.;Roethke, Theresa J.;Shu, Arthur;Stoy, Patrick;Ye, Guosen;Youngman, Mark;Lawhorn, Brian G.. And the article was included in Journal of Medicinal Chemistry in 2020.Formula: C7H3Cl2F3O2S This article mentions the following:

Investigation of TRPV4 as a potential target for the treatment of pulmonary edema associated with heart failure generated a novel series of acyclic amine inhibitors displaying exceptional potency and PK properties. The series arose through a scaffold hopping approach, which relied on use of an internal H-bond to replace a saturated heterocyclic ring. Optimization of the lead through investigation of both aryl regions revealed approaches to increase potency through substituents believed to enhance sep. intramol. and intermol. H-bond interactions. A proposed internal H-bond between the amine and neighboring benzenesulfonamide was stabilized by electronically modulating the benzenesulfonamide. In the aryl ether moiety, substituents para to the nitrile demonstrated an electronic effect on TRPV4 recognition. Finally, the acyclic amines inactivated CYP3A4 and this liability was addressed by modifications that sterically preclude formation of a putative metabolic intermediate complex to deliver advanced TRPV4 antagonists as leads for discovery of novel medicines. In the experiment, the researchers used many compounds, for example, 4-Chloro-2-(trifluoromethyl)benzene-1-sulfonyl chloride (cas: 54090-42-5Formula: C7H3Cl2F3O2S).

4-Chloro-2-(trifluoromethyl)benzene-1-sulfonyl chloride (cas: 54090-42-5) belongs to organic chlorides. An organic chloride is an organic compound containing at least one covalently bonded atom of chlorine. Their wide structural variety and divergent chemical properties lead to a broad range of names and applications.While alkyl bromides and iodides are more reactive, alkyl chlorides tend to be less expensive and more readily available. Alkyl chlorides readily undergo attack by nucleophiles.Formula: C7H3Cl2F3O2S

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

N-chlorosaccharin oxidation of propan-2-ol: a kinetic study was written by Singh, Sanjay K.;Arora, Monika;Kaur, Gurpreet;Kaur, Raman Deep;Gujral, Harjeet. And the article was included in Archives of Applied Science Research in 2010.Category: chlorides-buliding-blocks This article mentions the following:

Oxidation of propan-2-ol by N-chlorosaccharin (NCSA) in aqueous acetic acid medium has been carried out. The reactions exhibit first-order in oxidant and fractional order with substrate. The rate of oxidation increases with increase of acetic acid in medium while retarding by the addition of saccharin. This oxidation is acid catalyzed. The effect of temperature on reaction rate has also been studied. The thermodn. parameters have been calculated Based on all the kinetic data a possible operative mechanism has been proposed and a suitable rate law has been derived. In the experiment, the researchers used many compounds, for example, 2-Chlorobenzo[d]isothiazol-3(2H)-one 1,1-dioxide (cas: 14070-51-0Category: chlorides-buliding-blocks).

2-Chlorobenzo[d]isothiazol-3(2H)-one 1,1-dioxide (cas: 14070-51-0) belongs to organic chlorides. Organic chlorides are compounds containing a carbon-chlorine bond, which are widely used in the oil field as a wax dissolver. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control.Category: chlorides-buliding-blocks

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics