Endocytic Uptake of Self‐Assembled Iridium(III) Nanoaggregates for Holistic Treatment of Metastatic 3D Triple‐Negative Breast Tumor Spheroids DOI
Ayushi Chaudhary, Ashwini Kumar, Nirmal Keshari Swain

et al.

Small, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 28, 2024

Abstract Triple‐negative breast cancer (TNBC) presents a formidable challenge due to its aggressive behavior and limited array of treatment options available. This study focuses on employing nanoaggregate material organometallic Ir(III) complexes for treating TNBC cell line MDA‐MB‐231. In this approach, with enhanced cellular permeability are strategically designed achieved through the incorporation COOMe groups into their structure. The lead compound, IrL 1 , exhibits promiscuous nanoscale aggregation in RPMI culture media, characterized by stable hydrodynamic effective diameter ranging from 190 202 nm over 48 h. With excellent photo‐responsive contrast‐enhanced imaging properties an outstanding IC 50, 48h value 36.05± 0.03 n m when irradiated 390 light MDA‐MB‐231 (IC h Cisplatin is 5.29 µ ). cell, investigation confirms that nanoaggregates internalization via energy‐dependent endocytosis undergo ferroptosis ROS mediated death cells. Further, these vivo studies using NOD‐SCID mice confirmed tendency ablate tumors inoculated models at therapeutically relevant doses. Thus, comprehensive approach holds promise expanding repertoire adaptable characteristics, thereby advancing clinical utility nanomedicine holistic metastatic 3D triple‐negative tumor spheroids.

Language: Английский

Stereodivergent Synthesis of Spiroaminals via Chiral Bifunctional Hydrogen Bonding Organocatalysis DOI

Prasenjit Gayen,

Suman Sar,

Prasanta Ghorai

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(22)

Published: April 2, 2024

Spiroaminals represent novel structural motifs prevalent in diverse natural products and biologically active molecules. Achieving their enantioselective synthesis is a highly desirable challenging task synthetic endeavors due to intricate molecular frameworks. Herein, we accomplished the first stereodivergent construction of spiroaminals using chiral bifunctional organocatalyzed intramolecular 1,2-addition followed by an oxa-Michael addition cascade high atom step economical pathway. A proper modulation cinchona-derived squaramide catalysts efficiently provided access all possible stereoisomers with yield, diastereoselectivity, excellent enantioselectivity while displaying broad substrate tolerance. Additionally, validated scalability reaction demonstrated variable spiroaminal scaffolds, confirming viability our protocol.

Language: Английский

Citations

5
Intramolecular Cascade Cyclization of Cyclobutanone: Asymmetric Construction of Cyclobutanone Fused Oxa-Spirocycles DOI

Shibaram Panda,

Nikhil Dipak Chavan,

Prasanta Ghorai

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 8, 2025

The successful implementation of a cascade reaction involving cyclobutyl unit has posed significant challenge in achieving ring-retentive functionalization because the ring's sacrificial tendency. Herein, we have accomplished cinchona-derived squaramide-catalyzed sequence, encompassing desymmetrization cyclobutanone, followed by an aldol and, subsequently, 1,4-addition step. This overall process offers viable strategy to access architecturally fascinating oxa-spirocycles fused with cyclobutanone motifs good yields high optical purity.

Language: Английский

Citations

0
Asymmetric Aza-Michael/Michael/Mannich Domino Reaction of 2-Aminochalcones and 5-Alkenyl-Thiazolones: Access to Enantioenriched 1,4-Sulfur-Bridged Piperidinone Skeletons DOI
Zahid Khan,

Shweta Rohilla,

Vinod K. Singh

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 15, 2025

Herein, we disclose a novel organocatalytic approach for the enantioselective synthesis of 1,4-sulfur-bridged piperidinone skeletons via sequential aza-Michael/Michael/Mannich domino reaction 2-aminochalcones and 5-alkenyl-thiazolones. The one-pot catalyzed by bifunctional squaramide catalyst furnishes bridged polycyclic compounds with five contiguous stereocenters (three tertiary, two heteroquaternary) in excellent yields (up to 95%) stereochemical outcomes 99% ee up >20:1 dr). methodology offers outstanding control on regio- chemoselectivity, showcasing broad substrate compatibility. Additionally, is scalable postsynthetic transformation spirothiazolone-tetrahydroquinoline derivative further amplifies synthetic utility methodology.

Language: Английский

Citations

0
Enantioselective synthesis of spiro-N,O-ketals via iridium and Brønsted acid co-catalyzed asymmetric formal [4+2] cycloaddition DOI

Xiang-Qi Xie,

Xingguang Li, Pei Nian Liu

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(11), P. 1448 - 1451

Published: Jan. 1, 2024

An asymmetric formal [4+2] cycloaddition of cyclic enamides with 2-(1-hydroxyallyl)phenol via iridium and Brønsted acid co-catalysis has been achieved to afford chiral N -unsubstituted spiro- , O -ketals.

Language: Английский

Citations

3
An interrupted Heyns rearrangement approach for the regioselective synthesis of acylindoles DOI

Minakshi Altia,

Pazhamalai Anbarasan

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(92), P. 13747 - 13750

Published: Jan. 1, 2023

An efficient and general method for the synthesis of 2- 3-acylindoles has been achieved with high regioselectivity from o -acylanilines α-hydroxycarbonyl or its equivalent.

Language: Английский

Citations

7
Formal One Carbon Deletion of Indoline Hemiaminals under Tautomeric Control to Access 2-Aminobenzyl Compounds DOI
Keisuke Tokushige, Takumi Abe

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10349 - 10354

Published: July 1, 2024

Unprecedented tert-BuOK-mediated one carbon deletion of indoline hemiaminals has been achieved. This novel protocol provides an efficient synthetic tool for the construction 2-aminobenzyl compounds with high chemoselectivity. In addition, functionalized are difficult to make, which few limited means access currently exist. The key success is use in situ generated Heyns rearrangement products (α-amino carbonyl compounds) as precursors formal deletion.

Language: Английский

Citations

2
Regioselective synthesis of 2,3‐disubstituted indoles via interrupted Heyns rearrangement involving C‐C bond cleavage DOI

Minakshi Altia,

Pazhamalai Anbarasan

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(21)

Published: July 31, 2024

Abstract A novel metal free, Brønsted acid mediated and operationally simple strategy has been developed for regioselective synthesis of 2,3‐disubstituted indoles from α ‐hydroxyketones o ‐aminoaryl ketones in excellent yields. The reaction proceeds via interrupted Heyns rearrangement through the generation aminoenol intermediate followed by intramolecular trapping aromatization with C−C bond cleavage release corresponding ester. mechanism was further supported identification ester GCMS cyclic ‐hydroxydimethylketal, which afforded tethered indole derivative.

Language: Английский

Citations

2
Stereodivergent Synthesis of Spiroaminals via Chiral Bifunctional Hydrogen Bonding Organocatalysis DOI

Prasenjit Gayen,

Suman Sar,

Prasanta Ghorai

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: April 2, 2024

Abstract Spiroaminals represent novel structural motifs prevalent in diverse natural products and biologically active molecules. Achieving their enantioselective synthesis is a highly desirable challenging task synthetic endeavors due to intricate molecular frameworks. Herein, we accomplished the first stereodivergent construction of spiroaminals using chiral bifunctional organocatalyzed intramolecular 1,2‐addition followed by an oxa‐Michael addition cascade high atom step economical pathway. A proper modulation cinchona‐derived squaramide catalysts efficiently provided access all possible stereoisomers with yield, diastereoselectivity, excellent enantioselectivity while displaying broad substrate tolerance. Additionally, validated scalability reaction demonstrated variable spiroaminal scaffolds, confirming viability our protocol.

Language: Английский

Citations

1
Organocatalytic Desymmetric Double Aza-Michael Addition Cascade: Enantioselective Synthesis of Fused Morpholines DOI
Sachin S. Gorad, Prasanta Ghorai

Organic Letters, Journal Year: 2024, Volume and Issue: 26(26), P. 5571 - 5576

Published: June 26, 2024

Double aza-Michael addition (DAM) has become an emerging strategy for the construction of two carbon–nitrogen bonds in a single step, which can significantly simplify synthesis N-heterocycles. Hitherto, their asymmetric catalytic genre remains unattempted. Herein, we describe judicious design organocatalytic enantioselective desymmetric double cascade to access series functionalized fused morpholines with excellent yields and diastereo- enantioselectivities. A one-pot telescopic was demonstrated bridged triheterocyclic compound. In addition, scale-up various attractive postsynthetic modifications title products amplify significance current methodology.

Language: Английский

Citations

1
Reversal of Reactivity of Heyns Intermediate for the Concise Synthesis of Substituted 3-Hydroxyquinolines DOI

Minakshi Altia,

Pazhamalai Anbarasan

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16899 - 16908

Published: Nov. 4, 2024

An efficient and general method for the synthesis of 3-hydroxyquinolines has been achieved from o-acylanilines α-hydroxyketones in good yields. The strategy involves intramolecular reverse trapping situ generated aminoenol intermediate with an electrophilic carbonyl, viz. interrupted Heyns rearrangement, followed by aromatization. Important features include functional group tolerance, operational simplicity, gram-scale synthesis, broad synthetic utility.

Language: Английский

Citations

1