Category: 152213-63-3

On October 31, 2005, Segraves, Nathaniel L.; Crews, Phillip published an article.COA of Formula: C11H10BrNO2 The title of the article was Investigation of brominated tryptophan alkaloids from two Thorectidae sponges: Thorectandra and Smenospongia. And the article contained the following:

Chem. investigation of an NCI-DTP collection of Thorectandra sp. and a UCSC collection of Smenospongia sp. yielded six new brominated tryptophan derivatives : 6-bromo-1′-hydroxy-1′,8-dihydroaplysinopsin (e.g. IV), 6-bromo-1′-methoxy-1′,8-dihydroaplysinopsin (V), 6-bromo-1′-ethoxy-1′,8-dihydroaplysinopsin (VI), (-)-5-bromo-N,N-dimethyltryptophan (VII), (+)-5-bromohypaphorine (VIII), and 6-bromo-1H-indole-3-carboxylic acid Me ester (XI). Addnl., the known compounds aplysinopsin (I), 1′,8-dihydroaplysinopsin (II), 6-bromo-1′,8-dihydroaplysinopsin (III), (1H-indole-3-yl)acetic acid (IX), and (6-bromo-1H-indol-3-yl)acetic acid Me ester (X) were also encountered. The structures of IV-VIII and XI were confirmed on the basis of anal. of 1H and 13C (1D and 2D) NMR data as well as comparison to known compounds Compounds I, III-VIII, X, and XI were found to inhibit the growth of Staphylococcus epidermidis with either weak or moderate MICs. The experimental process involved the reaction of Methyl 2-(6-bromo-1H-indol-3-yl)acetate(cas: 152213-63-3).COA of Formula: C11H10BrNO2

The Article related to brominated tryptophan alkaloid thorectandra smenospongia antibacterial, Nonmammalian Biochemistry: Composition and Products and other aspects.COA of Formula: C11H10BrNO2

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

On October 31, 2005, Segraves, Nathaniel L.; Crews, Phillip published an article.COA of Formula: C11H10BrNO2 The title of the article was Investigation of brominated tryptophan alkaloids from two Thorectidae sponges: Thorectandra and Smenospongia. And the article contained the following:

Chem. investigation of an NCI-DTP collection of Thorectandra sp. and a UCSC collection of Smenospongia sp. yielded six new brominated tryptophan derivatives : 6-bromo-1′-hydroxy-1′,8-dihydroaplysinopsin (e.g. IV), 6-bromo-1′-methoxy-1′,8-dihydroaplysinopsin (V), 6-bromo-1′-ethoxy-1′,8-dihydroaplysinopsin (VI), (-)-5-bromo-N,N-dimethyltryptophan (VII), (+)-5-bromohypaphorine (VIII), and 6-bromo-1H-indole-3-carboxylic acid Me ester (XI). Addnl., the known compounds aplysinopsin (I), 1′,8-dihydroaplysinopsin (II), 6-bromo-1′,8-dihydroaplysinopsin (III), (1H-indole-3-yl)acetic acid (IX), and (6-bromo-1H-indol-3-yl)acetic acid Me ester (X) were also encountered. The structures of IV-VIII and XI were confirmed on the basis of anal. of 1H and 13C (1D and 2D) NMR data as well as comparison to known compounds Compounds I, III-VIII, X, and XI were found to inhibit the growth of Staphylococcus epidermidis with either weak or moderate MICs. The experimental process involved the reaction of Methyl 2-(6-bromo-1H-indol-3-yl)acetate(cas: 152213-63-3).COA of Formula: C11H10BrNO2

The Article related to brominated tryptophan alkaloid thorectandra smenospongia antibacterial, Nonmammalian Biochemistry: Composition and Products and other aspects.COA of Formula: C11H10BrNO2

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

On October 5, 2011, Isaji, Hisaaki; Nakazaki, Atsuo; Isobe, Minoru; Nishikawa, Toshio published an article.Reference of Methyl 2-(6-bromo-1H-indol-3-yl)acetate The title of the article was Concise synthesis of deformylflustrabromine, a marine indole alkaloid, through a 2-propynyl dicobalt hexacarbonyl complex. And the article contained the following:

Deformylflustrabromine, a marine indole alkaloid, was synthesized from 6-bromotryptamine, a plausible biosynthetic precursor, without protection of the amino group by a two-step reverse prenylation involving the Nicholas reaction and reductive decomplexation of the resulting acetylene dicobalt hexacarbonyl complex. The experimental process involved the reaction of Methyl 2-(6-bromo-1H-indol-3-yl)acetate(cas: 152213-63-3).Reference of Methyl 2-(6-bromo-1H-indol-3-yl)acetate

The Article related to deformylflustrabromine synthesis, Alkaloids: Alkaloids Containing One Nitrogen Atom In A Ring and other aspects.Reference of Methyl 2-(6-bromo-1H-indol-3-yl)acetate

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

Soto, Sara; Vaz, Esther; Dell’Aversana, Carmela; Alvarez, Rosana; Altucci, Lucia; de Lera, Angel R. published an article in 2012, the title of the article was New synthetic approach to paullones and characterization of their SIRT1 inhibitory activity.Category: indole-building-block And the article contains the following content:

A series of 7,12-dihydroindolo[3,2-d][1]benzazepine-6(5H)-ones (paullones) substituted at C9/C10 (Br) and C2 (Me, CF3, CO2Me) have been synthesized by a one-pot Suzuki-Miyaura cross-coupling of an o-aminoarylboronic acid and Me 2-iodoindoleacetate followed by intramol. amide formation. Other approaches to the paullone scaffold based on Pd-catalyzed C-H activation were unsuccessful. In vitro enzymic assay with recombinant human SIRT-1 indicated a strong inhibitory profile for the series, in particular the analog with a methoxycarbonyl group at C2 and a bromine at C9. These compounds are, in general, inducers of granulocyte differentiation of the U937 acute leukemia cell line and cause a marked increase in pre-G1 of the cell cycle. The experimental process involved the reaction of Methyl 2-(6-bromo-1H-indol-3-yl)acetate(cas: 152213-63-3).Category: indole-building-block

The Article related to aminoarylboronic acid iodoindoleacetate suzuki amidation, Heterocyclic Compounds (One Hetero Atom): Higher-Membered Rings and other aspects.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

On November 1, 2006, Baran, Phil S.; Shenvi, Ryan A. published an article.Application of 152213-63-3 The title of the article was Total Synthesis of (±)-Chartelline C. And the article contained the following:

The first total synthesis of (±)-chartelline C (I) in a concise 10-step sequence is reported. Highlights of the completion of this decades-old puzzle include (1) chemo- and position-selective installation of the heteroaromatic halogens, (2) halogen-sparing monoredn. of an alkyne linker, (3) a simple strategy for placement of the sensitive β-chloroenamide, (4) an unusually facile thermolysis of a vinyl carboxylic acid, and (5) a powerful ring contraction whose potential utility in heterocyclic chem. merits further investigation. The experimental process involved the reaction of Methyl 2-(6-bromo-1H-indol-3-yl)acetate(cas: 152213-63-3).Application of 152213-63-3

The Article related to chartelline c total synthesis, Alkaloids: Alkaloids Containing Three Or More Nitrogen Atoms and other aspects.Application of 152213-63-3

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

On April 7, 2022, Borjesson, Ulf; Perry, Matthew William Dampier; Grebner, Christoph; Michaelides, Iacovos Neal; Hayhow, Thomas George Christopher; Kettle, Jason Grant; Collie, Gavin William; Storer, Robert Ian; Bagal, Sharanjeet Kaur; Fallan, Charlene published a patent.Recommanded Product: Methyl 2-(6-bromo-1H-indol-3-yl)acetate The title of the patent was Synthesis of heterocyclic substituted pyrimidine anticancer agents. And the patent contained the following:

The synthesis of heterocyclic substituted pyrimidine anticancer agents I, wherein A is a protein binder unit; Z can be a bicyclic heterocyclic ring system with multiple heteroaroms N, O, S; Y can be a pyrimidine dione moiety; R can be a substituent on any available C or N such that alkyl, alkenyl, alkynyl or related groups with optional halo, nitrile, amino or similar groups; L, as a linker, can be an (un)saturated framework comprising C and H atoms and at least one heteroatom; and n can be an integer between 0-3 are prepared as pharmaceutically acceptable salts. Of note, II demonstrated a Cereblon HTRF IC50 binding of 2.1μM and can be employed in the treatment of cancers in humans or animals such that solid tumors, BRD4-sensitive tumors. The experimental process involved the reaction of Methyl 2-(6-bromo-1H-indol-3-yl)acetate(cas: 152213-63-3).Recommanded Product: Methyl 2-(6-bromo-1H-indol-3-yl)acetate

The Article related to heterocyclic pyrimidine anticancer preparation, Heterocyclic Compounds (More Than One Hetero Atom): Pyrimidines and Quinazolines and other aspects.Recommanded Product: Methyl 2-(6-bromo-1H-indol-3-yl)acetate

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

On July 24, 2014, Buckman, Brad Owen; Nicholas, John Beamond; Emayan, Kumaraswamy; Seiwert, Scott D.; Yuan, Shendong published a patent.Reference of Methyl 2-(6-bromo-1H-indol-3-yl)acetate The title of the patent was N-Heteroaryl carbamates as lysophosphatidic acid receptor antagonists and their preparation. And the patent contained the following:

Compounds of formula I, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or diagnose diseases, disorders, or conditions associated with one or more of the lysophosphatidic acid receptors are provided. Compounds of formula I wherein one of and B is acetylene and the other is (un)substituted 6- to 11-membered aryl, (un)substituted 5- to 11- membered heteroaryl, (un)substituted 4- to 11-membered heterocyclyl and (un)substituted 4- to 11-membered carbocyclyl; G is (un)substituted 6- to 11-membered aryl, (un)substituted 5- to 11- membered heteroaryl, (un)substituted 5- to 11-membered heterocyclyl and (un)substituted 5- to 11-membered carbocyclyl; D is OH, CO2H and derivatives, CONH2 and derivatives, azolyl, etc.; E is (un)substituted 6- to 10-membered arylene, (un)substituted 3- to 11-membered carbocyclyl, (un)substituted 3- to 11-membered heterocyclyl and (un)substituted 5- to 10-membered heteroarylene; J is (CR4R5)0-3; K is (CR2’R3′)n; M is (CR2R3)m; n and m are independently 0 – 3, provided that the sum of m + n is equal or greater than 1; L1 and L2 are independently a bond, CH2, CC, etc.; L3 is azolyl, thienyl, aminosulfonyl, etc.; L5 is single bond, CH=CH, CC, etc.; dashed bonds are single and double bonds; each Y is independently absent CR9, C(R9)2, N and NH, provided that only one of Y can be absent; R2, R2′, R3 and R3′ are independently H, halo, alkyl, haloalkyl, etc.; R4, R5 and R9 are independently H and (un)substituted alkyl; R4R5 or two adjacent R9 can be taken together to form (un)substituted cycloalkyl; and pharmaceutically acceptable salts thereof, are claimed. Example compound II was prepared by a multistep procedure (procedure given). The invention compounds were evaluated for their LPA antagonistic activity. From the assay, it was determined that compound II exhibited EC50 value in the range of greater than or equal to 50 nM and less than or equal to 500 nM. The experimental process involved the reaction of Methyl 2-(6-bromo-1H-indol-3-yl)acetate(cas: 152213-63-3).Reference of Methyl 2-(6-bromo-1H-indol-3-yl)acetate

The Article related to heteroaryl carbamate preparation lysophosphatidic acid receptor antagonist, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Reference of Methyl 2-(6-bromo-1H-indol-3-yl)acetate

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

On July 24, 2014, Buckman, Brad Owen; Nicholas, John Beamond; Emayan, Kumaraswamy; Seiwert, Scott D.; Yuan, Shendong published a patent.Reference of Methyl 2-(6-bromo-1H-indol-3-yl)acetate The title of the patent was N-Heteroaryl carbamates as lysophosphatidic acid receptor antagonists and their preparation. And the patent contained the following:

Compounds of formula I, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or diagnose diseases, disorders, or conditions associated with one or more of the lysophosphatidic acid receptors are provided. Compounds of formula I wherein one of and B is acetylene and the other is (un)substituted 6- to 11-membered aryl, (un)substituted 5- to 11- membered heteroaryl, (un)substituted 4- to 11-membered heterocyclyl and (un)substituted 4- to 11-membered carbocyclyl; G is (un)substituted 6- to 11-membered aryl, (un)substituted 5- to 11- membered heteroaryl, (un)substituted 5- to 11-membered heterocyclyl and (un)substituted 5- to 11-membered carbocyclyl; D is OH, CO2H and derivatives, CONH2 and derivatives, azolyl, etc.; E is (un)substituted 6- to 10-membered arylene, (un)substituted 3- to 11-membered carbocyclyl, (un)substituted 3- to 11-membered heterocyclyl and (un)substituted 5- to 10-membered heteroarylene; J is (CR4R5)0-3; K is (CR2’R3′)n; M is (CR2R3)m; n and m are independently 0 – 3, provided that the sum of m + n is equal or greater than 1; L1 and L2 are independently a bond, CH2, CC, etc.; L3 is azolyl, thienyl, aminosulfonyl, etc.; L5 is single bond, CH=CH, CC, etc.; dashed bonds are single and double bonds; each Y is independently absent CR9, C(R9)2, N and NH, provided that only one of Y can be absent; R2, R2′, R3 and R3′ are independently H, halo, alkyl, haloalkyl, etc.; R4, R5 and R9 are independently H and (un)substituted alkyl; R4R5 or two adjacent R9 can be taken together to form (un)substituted cycloalkyl; and pharmaceutically acceptable salts thereof, are claimed. Example compound II was prepared by a multistep procedure (procedure given). The invention compounds were evaluated for their LPA antagonistic activity. From the assay, it was determined that compound II exhibited EC50 value in the range of greater than or equal to 50 nM and less than or equal to 500 nM. The experimental process involved the reaction of Methyl 2-(6-bromo-1H-indol-3-yl)acetate(cas: 152213-63-3).Reference of Methyl 2-(6-bromo-1H-indol-3-yl)acetate

The Article related to heteroaryl carbamate preparation lysophosphatidic acid receptor antagonist, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Reference of Methyl 2-(6-bromo-1H-indol-3-yl)acetate

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

On November 2, 2016, Tian, Maoqun; Yan, Ming; Baran, Phil S. published an article.SDS of cas: 152213-63-3 The title of the article was 11-Step Total Synthesis of Araiosamines. And the article contained the following:

A concise route to a small family of exotic marine alkaloids known as the araiosamines has been developed, and their absolute configuration has been assigned. The dense array of functionality, high polarity, and rich stereochem. coupled with equilibrating topologies present an unusual challenge for chem. synthesis and an opportunity for innovation. Key steps involve the use of a new reagent for guanidine installation, a remarkably selective C-H functionalization, and a surprisingly simple final step that intersects a presumed biosynthetic intermediate. Synthetic araiosamines were shown to exhibit potency against Gram-pos. and -neg. bacteria despite a contrary report of no activity. The experimental process involved the reaction of Methyl 2-(6-bromo-1H-indol-3-yl)acetate(cas: 152213-63-3).SDS of cas: 152213-63-3

The Article related to araiosamine biomimetic preparation antibacterial gram pos neg, guanidinylation agent araiosamine preparation, carbon hydrogen bond functionalization araiosamine preparation and other aspects.SDS of cas: 152213-63-3

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

On September 29, 2011, Tajima, Nobumitsu; Yamashita, Atsuyuki; Kondo, Yurie; Chikamatsu, Kaori; Hiramatsu, Naoki; Makino, Mitsuhiro; Kitamoto, Katsunori; Kataoka, Daisuke; Nagai, Kazushige; Goto, Izumi; Torii, Masashi; Suzuki, Kimie; Iwai, Hisakazu; Hirooka, Hiroko published a patent.Safety of Methyl 2-(6-bromo-1H-indol-3-yl)acetate The title of the patent was Preparation of novel indole derivatives ad glucokinase activators. And the patent contained the following:

The providing of compound which has a glucokinase activating action. N-heterocyclyl-2-indolylproppanamide derivatives [I; a solid line with a —- line = a single bond or a double bond; X-C-Y with a —- line = N-C:C or C:C-N; R1 = H, C1-6 alkyl, C2-6 alkenyl, C1-6 alkylsulfonyl, C1-6 alkyl-arylsulfonyl, arylsulfonyl, alkanoyl, aroyl, C1-6 alkylsulfonyl-aralkyl, aralkyl, alkanoylaryl, aryl, carboxyl-C1-6 alkyl, halo-C1-6 alkyl, hydroxy-C1-6 alkyl, amino-C1-6 alkyl, carbamoyl-C1-6 alkyl, etc.; R2 = H, C1-6 alkyl; R3 = C1-6 alkyl, C3-7 cycloalkyl, heteroaryl; R4 = H, halo, NO2; R5 = H, C1-6 alkyl, halo, aryl, C1-6 alkoxy, aralkyloxy, aroyl, alkanoyl; R6 = H, halo, alkanoyl-aryl, aryl, HO, aralkyloxy, C1-6 alkoxy, alkanoyl-C1-6 alkoxy, aroyl-C1-6 alkoxy, alkanoylaryloxy, aryloxy, NO2, alkanoyl, (un)substituted aroyl, CO2H, C1-6 alkoxycarbonyl, heteroaryl, aryl-C1-6 alkyl, aryl-hydroxy-C1-6 alkyl, etc.; R7 = H, C1-6 alkyl, halo, alkanoyl; R1 and R7 together with X-C-C to which they are attached form cyclohexanone ring; A ring = 5- or 6-membered monocyclic N-containing heterocyclyl optionally containing addnl. N or S which optionally fused to aryl or C5-7 cycloalkyl to form bicyclic heterocyclic ring, in particular thiazolyl, pyridyl, or benzothiazolyl; R8 = H, halo, NO2, cyano, C1-6 alkoxycarbonyl, aralkyloxycarbonyl, HO, CO2H, (un)substituted CONH2, carboxy-C1-6 alkyl, etc. ] or prodrugs thereof or pharmaceutically acceptable salts thereof. These compounds have glucokinase activating activity and are useful for the prevention or treatment of diabetes or diabetes complications such as diabetic retinopathy, diabetic nephropathy, diabetic neuropathy, ischemic heart diseases, or arteriosclerosis. Thus, 9.4 mg 2-(6-acetyl-5-fluoro-1-methyl-1H-indol-3-yl)-3-cyclopentylpropionic acid was dissolved in 1.5 mL DMF , treated with 86.3 mg 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 48.6 mg 1-hydroxy-1H-benzotriazole monohydrate, stirred at room temperature for 2 h, treated with 178 mg 1-[2-(2-Aminothiazol-4-yl)acetyl]piperidine-4-carboxylic acid Et ester, stirred at 70° for 20 h to give, after workup and thin layer silica gel chromatog., 93% 1-[2-[2-[[2-(6-acetyl-5-fluoro-1-methyl-1H-indol-3-yl)-3-cyclopentylpropionyl]amino]thiazol-4-yl]acetyl]piperidine-4-carboxylic acid Et ester (II). II and compound (III) activated human glucokinase by 539 and 1,048 fold, resp., in in vitro phosphorylation of D-glucose with ATP. The experimental process involved the reaction of Methyl 2-(6-bromo-1H-indol-3-yl)acetate(cas: 152213-63-3).Safety of Methyl 2-(6-bromo-1H-indol-3-yl)acetate

The Article related to indole preparation prevention treatment diabetes, diabetes complication prevention treatment indole preparation, heterocyclylindolylproppanamide preparation glucokinase activator, pyridylindolylcyclopentylpropanamide preparation glucokinase activator and other aspects.Safety of Methyl 2-(6-bromo-1H-indol-3-yl)acetate

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