Month: February 2023

Relation of chemical structure to plant growth-regulator activity in the pineapple plant. V. Post-harvest delay of senescence of pineapple fruit was written by Gortner, Willis A.;Leeper, Robert W.. And the article was included in Botanical Gazette (Chicago) in 1969.Formula: C11H11NO2 This article mentions the following:

The effects of 369 compounds, including 94 phenoxyacetic acids, 43 other phenoxy acids, 23 phenylacetic acids, 15 hydrocinnamic acids, 9 benzoic acids, 7 salicylic acids, 48 naphthalene derivatives, 22 indole acids, 5 hydrazine derivatives, and 8 cinnamic acids, for postharvest delay of senescence of pineapple fruit (Ananas comosus) were determined Seventy-six of the compounds were active, and 27 were highly active in delaying senescence. In the phenoxyacetic acid series, high activity was obtained from some halogen-substituted acids but not generally from Me-substituted acids. In the phenoxy-α-propionic acid series, high activity was not observed for a number of halogen- and Me-substituted acids. None of the substituted phenoxy acids other than HOAc and α- propionic showed even moderate activity. An appreciable number of Cl-substituted phenylacetic acids and several benzoic acids showed activity. None of the phenylalkylcarboxylic acids other than HOAc showed even moderate activity. None of the salicylic acid, phthalic acids, or phthalamic acids showed any activity. All hydrazine derivatives were inactive. In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1Formula: C11H11NO2).

3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Formula: C11H11NO2

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Synthesis and screening of 3-[N-substituted phenylamino-2-phenyl-4-thiazolidinon-5-ylidene]-1,3-dihydro-indol-2-ones for in vivo anti-inflammatory activity was written by Devi, N. Saritha;Srinivas, B.;Sarangapani, Manda. And the article was included in Journal of Pharmaceutical Sciences and Research in 2019.Formula: C8H4N2O4 This article mentions the following:

A novel 3-[N-substituted phenylamino-2-phenyl-4-thiazolidinon-5-ylidene]-1,3-dihydro-indol-2-ones I (R = H, 5-F, 7-Me) was synthesized by condensation of isatins II with 2-phenyl-3-(phenylamino)-1,3-thiazolidin-4-one. The compounds I (5-Cl, 7-Cl, 5-F, 5-Br, 5,6-Cl₂, 5-OH) evaluated for in vivo anti-inflammatory activity. The compound I (R = 5,6-Cl₂) showed more in vivo anti-inflammatory activity with 72.5% of inhibition among test compounds The compounds I (R = 5-F, 5Cl, 5-Br, 7-Cl,5-OH) were next in the order of exhibiting in vivo anti-inflammatory activity with 65.75, 63.0, 61.25, 52.5 and 51.25% resp., when compared to standard drug Indomethacin with 73.7% of inhibition. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Formula: C8H4N2O4).

7-Nitroindoline-2,3-dione (cas: 112656-95-8) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Formula: C8H4N2O4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Indolylalkyltriphenylphosphonium Analogues Are Membrane-Depolarizing Mycobactericidal Agents was written by Li, Ming;Nyantakyi, Samuel A.;Gopal, Pooja;Aziz, Dinah binte;Dick, Thomas;Go, Mei-Lin. And the article was included in ACS Medicinal Chemistry Letters in 2017.Recommanded Product: 4769-96-4 This article mentions the following:

Agents that selectively target the mycobacterial membrane could potentially shorten treatment time for tuberculosis, reduce relapse and curtail emergence of resistant strains. The lipophilicity and extensive charge delocalized state of the triphenylphosphonium (TPP) cation strongly favor accumulation within bacterial membranes. Here we explored the antimycobacterial activities and membrane targeting properties of indolylalkyltriphenylphosphonium analogs. The most active analogs preferentially inhibited growth of Mycobacterium tuberculosis H37Rv (MIC₅₀ 2-4 μM) and were cidal against Mycobacterium bovis BCG (MBC99 3 μM). In spite of their propensity to accumulate within membranes, we found no evidence that these compounds permeabilized mycobacterial membranes or induced cell-envelope stress. Our investigations indicated that the cidal effects of these compounds stem from sustained depolarization of mycobacterial membranes and ensuing disruptive effects on electron transfer and cell division. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Recommanded Product: 4769-96-4).

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 4769-96-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Organocatalytic Enantioselective Sulfenylation of β-Keto Phosphonates: A Convenient Approach to Construct Hetero-Quaternary Stereocenters was written by Lin, Aijun;Fang, Ling;Zhu, Xi;Zhu, Chengjian;Cheng, Yixiang. And the article was included in Advanced Synthesis & Catalysis in 2011.Reference of 14204-27-4 This article mentions the following:

The highly effective and enantioselective sulfenylation of β-keto phosphonates catalyzed by α,α-diaryl-L-prolinols has been developed. The optically active α-sulfenylated β-keto phosphonates could be obtained under mild reaction conditions in good yields (up to 92%) and with excellent enantioselectivities (up to 92% ee). In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Reference of 14204-27-4).

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Reference of 14204-27-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Antiadhesion Therapy for Urinary Tract Infections-A Balanced PK/PD Profile Proved To Be Key for Success was written by Jiang, Xiaohua;Abgottspon, Daniela;Kleeb, Simon;Rabbani, Said;Scharenberg, Meike;Wittwer, Matthias;Haug, Martina;Schwardt, Oliver;Ernst, Beat. And the article was included in Journal of Medicinal Chemistry in 2012.Reference of 754214-56-7 This article mentions the following:

The initial step for the successful establishment of urinary tract infections (UTIs), predominantly caused by uropathogenic Escherichia coli, is the adhesion of bacteria to urothelial cells. This attachment is mediated by FimH, a mannose-binding adhesin, which is expressed on the bacterial surface. To date, UTIs are mainly treated with antibiotics, leading to the ubiquitous problem of increasing resistance against most of the currently available antimicrobials. Therefore, new treatment strategies are urgently needed, avoiding selection pressure and thereby implying a reduced risk of resistance. Here, we present a new class of highly active antimicrobials, targeting the virulence factor FimH. When the most potent representative, an indolinylphenyl mannoside, was administered in a mouse model at the low dosage of 1 mg/kg (corresponding to approx. 25 μg/mouse), the minimal therapeutic concentration to prevent UTI was maintained for more than 8 h. In a treatment study, the colony-forming units in the bladder could be reduced by almost 4 orders of magnitude, comparable to the standard antibiotic treatment with ciprofloxacin (8 mg/kg, s.c.). In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7Reference of 754214-56-7).

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Reference of 754214-56-7

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Electrochemically Enabled C3-Formylation and -Acylation of Indoles with Aldehydes was written by Yang, Liquan;Liu, Zhaoran;Li, Yujun;Lei, Ning;Shen, Yanling;Zheng, Ke. And the article was included in Organic Letters in 2019.Category: indole-building-block This article mentions the following:

Reported herein is an effective strategy for oxidative cross-coupling of indoles with various aldehydes. The strategy is based on a two-step transformation via a known Mannich-type reaction and a C-N bond cleavage for carbonyl introduction. The key step-the C-N bond cleavage of the Mannich product-was enabled by electrochem. This strategy (with over 40 examples) ensures excellent functional-group tolerance as well as late-stage functionalization of pharmaceutical mols. In the experiment, the researchers used many compounds, for example, 1,4-Dimethyl-1H-indole-3-carbaldehyde (cas: 170489-16-4Category: indole-building-block).

1,4-Dimethyl-1H-indole-3-carbaldehyde (cas: 170489-16-4) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Category: indole-building-block

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Sulfenamide-enabled ortho thiolation of aryl iodides via palladium/norbornene cooperative catalysis was written by Li, Renhe;Zhou, Yun;Yoon, Ki-Young;Dong, Zhe;Dong, Guangbin. And the article was included in Nature Communications in 2019.SDS of cas: 14204-27-4 This article mentions the following:

A general ortho thiolation of common aryl and heteroaryl iodides RI (R = 2-methylphenyl, 1-naphthyl, quinolin-5-yl, etc.) via palladium-norbornene cooperative catalysis is reported. Using this approach, an aryl or alky sulfur moiety can be site-selectively introduced at the arene ortho position without using sterically or electronically biased substrates. The arene ipso functionalization is simultaneously achieved through Heck, Suzuki or Sonogashira termination. The reaction is enabled by a unique class of electrophiles in palladium-norbornene cooperative catalysis, which are sulfenamides such as N-phenyl-N-(phenylsulfanyl)formamide, 1-(phenylsulfanyl)pyrrolidin-2-one, 1-(phenylsulfanyl)azepan-2-one, etc. derived from seven-membered lactams. The broad substrates scope and high chemoselectivity could make this method attractive for synthesis of complex sulfur-containing aromatic compounds, e.g., I. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4SDS of cas: 14204-27-4).

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.SDS of cas: 14204-27-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Catalyst-free synthesis of α¹-oxindole-α-hydroxyphosphonates via phospha-aldol reaction of isatins employing N-heterocyclic phosphine (NHP)-thiourea was written by Molleti, Nagaraju;Yong Kang, Jun. And the article was included in Organic & Biomolecular Chemistry in 2016.Quality Control of 5,6-Difluoroindoline-2,3-dione This article mentions the following:

A highly efficient phospha-aldol reaction for the synthesis of α¹-oxindole-α-hydroxyphosphonates is developed using N-heterocyclic phosphine (NHP)-thiourea as a phosphonylation reagent under catalyst, additive free conditions. This methodol. encompasses a variety of isatin derivatives to provide α¹-oxindole- α-hydroxyphosphonates up to 99% yield. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Quality Control of 5,6-Difluoroindoline-2,3-dione).

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Quality Control of 5,6-Difluoroindoline-2,3-dione

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Cu(I)-catalyzed intramolecular cyclization of ene-carbamates: synthesis of indoles and pyrrolo[2,3-c]pyridines was written by Barberis, Claude;Gordon, Thomas D.;Thomas, Christine;Zhang, Xiaolei;Cusack, Kevin P.. And the article was included in Tetrahedron Letters in 2005.Name: Methyl 5-fluoro-1H-indole-2-carboxylate This article mentions the following:

Over the past few years, the use of palladium-catalyzed aromatic carbon-nitrogen bond forming reactions by the cross-coupling of aryl halides or triflates and amines has become a useful synthetic tool. Herein, a copper(I) catalyst system that allows efficient synthesis of functionalized indoles and pyrrolo[2,3-c]pyridine derivatives was described. This method takes advantage of amino acid promoted copper coupling of amines with aryl halides, in particular, the use of the CuI/L-proline catalyst system. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Name: Methyl 5-fluoro-1H-indole-2-carboxylate).

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Name: Methyl 5-fluoro-1H-indole-2-carboxylate

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Iridium-Catalyzed, Weakly Coordination-Assisted Ortho-Alkynylation of (Hetero)aromatic Carboxylic Acids without Cyclization was written by Chen, Changpeng;Liu, Pei;Tang, Jinghua;Deng, Gongda;Zeng, Xiaoming. And the article was included in Organic Letters in 2017.Product Details of 1912-45-4 This article mentions the following:

In the presence of [Cp^*IrCl₂]₂, arylcarboxylic acids and arylacetic acids such as 2-methylbenzoic acid or o-methylphenylacetic acid underwent regioselective directed alkynylation with i-Pr₃SiCCBr mediated by KHCO₃ and air in tert-amyl alc. to yield alkynylbenzoic acids and alkynylphenylacetic acids such as I (X = bond, CH₂) in 32-96% yields. Indolyl- and thienyl carboxylic and acetic acids and benzothiopheneacetic acids also underwent regioselective alkynylation. The reaction mechanism was studied using the alkynylation of potassium 2-methylbenzoate without added KHCO₃, deuterium labeling experiments, and the kinetic isotope effects on alkynylation. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Product Details of 1912-45-4).

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Product Details of 1912-45-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles