151.14 | - Indole Building Blocks

Ramaraju, Panduga et al. published their research in European Journal of Organic Chemistry in 2017 | CAS: 56341-41-4

5-Fluoroindolin-2-one (cas: 56341-41-4) 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. 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.Electric Literature of C8H6FNO

An Unprecedented Pseudo-[3+2] Annulation between N-(4-Methoxyphenyl)aldimines and Aqueous Glutaraldehyde: Direct Synthesis of Pyrrole-2,4-dialdehydes was written by Ramaraju, Panduga;Mir, Nisar A.;Singh, Deepika;Sharma, Preetika;Kant, Rajni;Kumar, Indresh. And the article was included in European Journal of Organic Chemistry in 2017.Electric Literature of C8H6FNO This article mentions the following:

A new method for the direct one-pot synthesis of substituted pyrrole-2,4-dialdehdyes was developed. This overall pseudo-[3+2]-annulation reaction between glutaraldehyde and N-(4-methoxyphenyl)aldimines proceeds through proline-catalyzed direct Mannich reaction/cyclization, followed by 2-iodoxybenzoic acid mediated oxidative rearrangement of the in situ generated intermediate to give pyrrole-2,4-dialdehydes in high yields (up to 80 %). In the experiment, the researchers used many compounds, for example, 5-Fluoroindolin-2-one (cas: 56341-41-4Electric Literature of C8H6FNO).

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

Senwar, Kishna Ram et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2016 | CAS: 56341-41-4

5-Fluoroindolin-2-one (cas: 56341-41-4) 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. 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). Application of 56341-41-4

Design and synthesis of 4′-O-alkylamino-tethered-benzylideneindolin-2-ones as potent cytotoxic and apoptosis inducing agents was written by Senwar, Kishna Ram;Reddy, T. Srinivasa;Thummuri, Dinesh;Sharma, Pankaj;Bharghava, Suresh K.;Naidu, V. G. M.;Shankaraiah, Nagula. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2016.Application of 56341-41-4 This article mentions the following:

A series of new 4′-O-alkylamino-tethered-benzylideneindolin-2-one derivatives was synthesized and evaluated for their anti-proliferative activity against selected human cancer cell lines of lung (A549), prostate (DU-145), breast (BT549 and MDA-MB-231) and normal breast epithelial cells (MCF-10 脜). Gratifyingly, the compounds (Z)-5-chloro-3-(4′-(3-(2,6-dimethylmorpholino)propoxy)-3′-methoxybenzylidene)indolin-2-one , (Z)-5-chloro-3-(3′-methoxy-4′-(3-(4-(3-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)propoxy)benzylidene)indolin-2-one and (Z)-5-chloro-3-(3′-methoxy-4′-(3-(4-methylpiperazin-1-yl)propoxy)benzylidene)indolin-2-one exhibited potent cytotoxicity against breast cancer cell lines (BT549 and MDA-MB-231) with IC₅₀ values at 1.26-2.77 渭M, and are safer with lesser cytotoxicity on normal breast epithelial cells (MCF-10 脜). Further, experiments were conducted with these compounds (Z)-5-chloro-3-(4′-(3-(2,6-dimethylmorpholino)propoxy)-3′-methoxybenzylidene)indolin-2-one, (Z)-5-chloro-3-(3′-methoxy-4′-(3-(4-(3-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)propoxy)benzylidene)indolin-2-one and (Z)-5-chloro-3-(3′-methoxy-4′-(3-(4-methylpiperazin-1-yl)propoxy)benzylidene)indolin-2-one on MDA-MB-231 cancer cells to study the mechanism of growth inhibition and apoptosis inducing effect. Treatment of MDA-MB-231 cells with test compounds resulted in inhibition of cell migration through disorganization and disruption of F-actin capping protein. The flow-cytometry anal. results showed that the compound (Z)-5-Chloro-3-(3′-methoxy-4′-(3-(4-(3-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)propoxy)benzylidene)indolin-2-one arrested MDA-MB-231 cells in G0/G1 phase of cell cycle in a dose dependent manner. Hoechst staining study revealed that the test compounds inhibited tumor cell proliferation through induction of apoptosis. In addition, the mitochondrial membrane potential (D唯m) was affected and the increased level of reactive oxygen species (ROS) was noted in MDA-MB-231 cells. In the experiment, the researchers used many compounds, for example, 5-Fluoroindolin-2-one (cas: 56341-41-4Application of 56341-41-4).

Tian, Shaixiao et al. published their research in Synlett in 2018 | CAS: 56341-41-4

5-Fluoroindolin-2-one (cas: 56341-41-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Recommanded Product: 5-Fluoroindolin-2-one

The Application of Vinamidinium Salt to the Synthesis of 3-Chloro-伪-carbolines was written by Tian, Shaixiao;Mao, Yu;Jiang, Yongjun;Xu, Guangyu. And the article was included in Synlett in 2018.Recommanded Product: 5-Fluoroindolin-2-one This article mentions the following:

A convenient synthesis of 3-chloro-伪-carbolines, e.g., I by the condensation of vinamidinium salt with 2-indolinones via two steps is reported. This protocol has the advantages of readily available starting materials, high yields and easy workup. In the experiment, the researchers used many compounds, for example, 5-Fluoroindolin-2-one (cas: 56341-41-4Recommanded Product: 5-Fluoroindolin-2-one).

Zhang, Lingjuan et al. published their research in Applied Catalysis, B: Environmental in 2023 | CAS: 56341-41-4

5-Fluoroindolin-2-one (cas: 56341-41-4) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Computed Properties of C8H6FNO

Tuning band structures of Hf-PCN-224(M) for 尾-Carbonyl C(sp³)-H bond activation and difunctionalization: Tandem C(sp³) radical cross-coupling through photoredox was written by Zhang, Lingjuan;Ma, Lijuan;Yuan, Jincong;Zhang, Xian-Ming;Tang, Zhiyong. And the article was included in Applied Catalysis, B: Environmental in 2023.Computed Properties of C8H6FNO This article mentions the following:

The construction of C(sp³)-C(sp³) bonds by different C(sp³) radicals coupling reactions is still unexplored due to the high bond dissociation energy of C(sp³)-H bond and the difficulty for selective generating of C(sp³) radical. Benefiting from the precisely regulating for band structures of Hf-PCN-224(M), the 尾-carbonyl C(sp³)-H bonds are effectively oxidized by photo-generated holes to affording C(sp³) radicals in this work. C(sp³)-C(sp³) and C(sp³)-O bonds are constructed by tandem radical-radical cross-coupling, hydrogen atom transfer (HAT), and radical-radical cross-coupling between two C(sp³)-H bonds, enabling an effective C3-difunctionalization of indolin-2-ones under photo-thermo synergetic catalysis on Hf-PCN-224(Cu). Significantly, OH serves as triple roles, introduced hydroxyl group in situ, HAT abstractor and 伪-heteroatom for secondary activating C(sp³)-H bonds. Control experiments, EPR spectroscopy and DFT calculation provide insight into the tandem radicals cross-coupling mechanism. This operable strategy opens up a door for the difunctionalization of C(sp³)-H bonds in heterogeneous photoredox manner. In the experiment, the researchers used many compounds, for example, 5-Fluoroindolin-2-one (cas: 56341-41-4Computed Properties of C8H6FNO).

Senwar, Kishna Ram et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2016 | CAS: 56341-41-4

A series of new 4′-O-alkylamino-tethered-benzylideneindolin-2-one derivatives was synthesized and evaluated for their anti-proliferative activity against selected human cancer cell lines of lung (A549), prostate (DU-145), breast (BT549 and MDA-MB-231) and normal breast epithelial cells (MCF-10 Å). Gratifyingly, the compounds (Z)-5-chloro-3-(4′-(3-(2,6-dimethylmorpholino)propoxy)-3′-methoxybenzylidene)indolin-2-one , (Z)-5-chloro-3-(3′-methoxy-4′-(3-(4-(3-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)propoxy)benzylidene)indolin-2-one and (Z)-5-chloro-3-(3′-methoxy-4′-(3-(4-methylpiperazin-1-yl)propoxy)benzylidene)indolin-2-one exhibited potent cytotoxicity against breast cancer cell lines (BT549 and MDA-MB-231) with IC₅₀ values at 1.26-2.77 μM, and are safer with lesser cytotoxicity on normal breast epithelial cells (MCF-10 Å). Further, experiments were conducted with these compounds (Z)-5-chloro-3-(4′-(3-(2,6-dimethylmorpholino)propoxy)-3′-methoxybenzylidene)indolin-2-one, (Z)-5-chloro-3-(3′-methoxy-4′-(3-(4-(3-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)propoxy)benzylidene)indolin-2-one and (Z)-5-chloro-3-(3′-methoxy-4′-(3-(4-methylpiperazin-1-yl)propoxy)benzylidene)indolin-2-one on MDA-MB-231 cancer cells to study the mechanism of growth inhibition and apoptosis inducing effect. Treatment of MDA-MB-231 cells with test compounds resulted in inhibition of cell migration through disorganization and disruption of F-actin capping protein. The flow-cytometry anal. results showed that the compound (Z)-5-Chloro-3-(3′-methoxy-4′-(3-(4-(3-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)propoxy)benzylidene)indolin-2-one arrested MDA-MB-231 cells in G0/G1 phase of cell cycle in a dose dependent manner. Hoechst staining study revealed that the test compounds inhibited tumor cell proliferation through induction of apoptosis. In addition, the mitochondrial membrane potential (DΨm) was affected and the increased level of reactive oxygen species (ROS) was noted in MDA-MB-231 cells. In the experiment, the researchers used many compounds, for example, 5-Fluoroindolin-2-one (cas: 56341-41-4Application of 56341-41-4).

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

Tian, Shaixiao et al. published their research in Synlett in 2018 | CAS: 56341-41-4

The Application of Vinamidinium Salt to the Synthesis of 3-Chloro-α-carbolines was written by Tian, Shaixiao;Mao, Yu;Jiang, Yongjun;Xu, Guangyu. And the article was included in Synlett in 2018.Recommanded Product: 5-Fluoroindolin-2-one This article mentions the following:

A convenient synthesis of 3-chloro-α-carbolines, e.g., I by the condensation of vinamidinium salt with 2-indolinones via two steps is reported. This protocol has the advantages of readily available starting materials, high yields and easy workup. In the experiment, the researchers used many compounds, for example, 5-Fluoroindolin-2-one (cas: 56341-41-4Recommanded Product: 5-Fluoroindolin-2-one).

Zhang, Lingjuan et al. published their research in Applied Catalysis, B: Environmental in 2023 | CAS: 56341-41-4

Tuning band structures of Hf-PCN-224(M) for β-Carbonyl C(sp³)-H bond activation and difunctionalization: Tandem C(sp³) radical cross-coupling through photoredox was written by Zhang, Lingjuan;Ma, Lijuan;Yuan, Jincong;Zhang, Xian-Ming;Tang, Zhiyong. And the article was included in Applied Catalysis, B: Environmental in 2023.Computed Properties of C8H6FNO This article mentions the following:

The construction of C(sp³)-C(sp³) bonds by different C(sp³) radicals coupling reactions is still unexplored due to the high bond dissociation energy of C(sp³)-H bond and the difficulty for selective generating of C(sp³) radical. Benefiting from the precisely regulating for band structures of Hf-PCN-224(M), the β-carbonyl C(sp³)-H bonds are effectively oxidized by photo-generated holes to affording C(sp³) radicals in this work. C(sp³)-C(sp³) and C(sp³)-O bonds are constructed by tandem radical-radical cross-coupling, hydrogen atom transfer (HAT), and radical-radical cross-coupling between two C(sp³)-H bonds, enabling an effective C3-difunctionalization of indolin-2-ones under photo-thermo synergetic catalysis on Hf-PCN-224(Cu). Significantly, OH serves as triple roles, introduced hydroxyl group in situ, HAT abstractor and α-heteroatom for secondary activating C(sp³)-H bonds. Control experiments, EPR spectroscopy and DFT calculation provide insight into the tandem radicals cross-coupling mechanism. This operable strategy opens up a door for the difunctionalization of C(sp³)-H bonds in heterogeneous photoredox manner. In the experiment, the researchers used many compounds, for example, 5-Fluoroindolin-2-one (cas: 56341-41-4Computed Properties of C8H6FNO).

Zhang, Lingjuan et al. published their research in Applied Catalysis, B: Environmental in 2023 | CAS: 56341-41-4

The construction of C(sp³)-C(sp³) bonds by different C(sp³) radicals coupling reactions is still unexplored due to the high bond dissociation energy of C(sp³)-H bond and the difficulty for selective generating of C(sp³) radical. Benefiting from the precisely regulating for band structures of Hf-PCN-224(M), the β-carbonyl C(sp³)-H bonds are effectively oxidized by photo-generated holes to affording C(sp³) radicals in this work. C(sp³)-C(sp³) and C(sp³)-O bonds are constructed by tandem radical-radical cross-coupling, hydrogen atom transfer (HAT), and radical-radical cross-coupling between two C(sp³)-H bonds, enabling an effective C3-difunctionalization of indolin-2-ones under photo-thermo synergetic catalysis on Hf-PCN-224(Cu). Significantly, OH serves as triple roles, introduced hydroxyl group in situ, HAT abstractor and α-heteroatom for secondary activating C(sp³)-H bonds. Control experiments, EPR spectroscopy and DFT calculation provide insight into the tandem radicals cross-coupling mechanism. This operable strategy opens up a door for the difunctionalization of C(sp³)-H bonds in heterogeneous photoredox manner. In the experiment, the researchers used many compounds, for example, 5-Fluoroindolin-2-one (cas: 56341-41-4Computed Properties of C8H6FNO).

Tian, Shaixiao et al. published their research in Synlett in 2018 | CAS: 56341-41-4

Zhang, Lingjuan et al. published their research in Applied Catalysis, B: Environmental in 2023 | CAS: 56341-41-4

The construction of C(sp³)-C(sp³) bonds by different C(sp³) radicals coupling reactions is still unexplored due to the high bond dissociation energy of C(sp³)-H bond and the difficulty for selective generating of C(sp³) radical. Benefiting from the precisely regulating for band structures of Hf-PCN-224(M), the β-carbonyl C(sp³)-H bonds are effectively oxidized by photo-generated holes to affording C(sp³) radicals in this work. C(sp³)-C(sp³) and C(sp³)-O bonds are constructed by tandem radical-radical cross-coupling, hydrogen atom transfer (HAT), and radical-radical cross-coupling between two C(sp³)-H bonds, enabling an effective C3-difunctionalization of indolin-2-ones under photo-thermo synergetic catalysis on Hf-PCN-224(Cu). Significantly, OH serves as triple roles, introduced hydroxyl group in situ, HAT abstractor and α-heteroatom for secondary activating C(sp³)-H bonds. Control experiments, EPR spectroscopy and DFT calculation provide insight into the tandem radicals cross-coupling mechanism. This operable strategy opens up a door for the difunctionalization of C(sp³)-H bonds in heterogeneous photoredox manner. In the experiment, the researchers used many compounds, for example, 5-Fluoroindolin-2-one (cas: 56341-41-4Computed Properties of C8H6FNO).