110166-72-8Relevant academic research and scientific papers
Synthesis of 11,12-dihydro benzo[c]phenanthridines via a Pd-catalyzed unusual construction of isocoumarin ring/FeCl3-mediated intramolecular arene-allyl cyclization: First identification of a benzo[c]phenanthridine based PDE4 inhibitor
Ghule, Shailendra S.,Hossain, Kazi Amirul,Kumar, Jetta Sandeep,Mathew, Jessy E.,Mounika, Guntipally,Mudgal, Jayesh,Pal, Manojit,Parsa, Kishore V. L.,Reddy, Gangireddy Sujeevan,Shenoy, Gautham G.,Thirupataiah, B.
, (2020)
In spite of their various pharmacological properties the anti-inflammatory potential of benzo[c]phenanthridines remained underexplored. Thus, for the first time PDE4 inhibitory potential of 11,12-dihydro benzo[c]phenanthridine/benzo[c]phenanthridine was a
Ultrasound assisted Cu-catalyzed decarbonylative Sonogashira coupling-cyclization strategy: Synthesis and evaluation of 3-heteroarylmethylene isoindolin-1-ones against SIRT1
Ganapathisivaraja, P.,Kapavarapu, Ravikumar,Pal, Manojit,Praneeth, Muthineni Sai,Ramarao, Abburi,Rao, G. Venkata Nageswara,Rao, Mandava V. Basaveswara,Tej, Mandava Bhuvan
, (2021/11/08)
Prompted by the reported HDAC1 inhibition / anticancer properties of 3-methyleneisoindolin-1-one derivatives a series of 3-heteroarylmethylene substituted isoindolin-1-ones were explored as potential inhibitors of SIRT1. A sonochemical approach based on the Cu(I)-catalyzed decarbonylative Sonogashira coupling-cyclization strategy was developed for accessing this class of compounds. The approach involved a faster and milder synthesis of 3-heteroarylmethylene isoindolin-1-ones with high regioselectivity via cross-coupling of 2-iodobenzamides with heteroaryl alkynyl acids followed by 5-exo-dig heteroannulation in the same pot. The methodology was latter extended to the synthesis of 3-arylmethylene isoindolin-1-ones when the desired products were obtained in acceptable yield. When tested for the SIRT1 inhibitory potential in vitro some of the 3-heteroarylmethylene isoindolin-1-ones showed good activities with the compound 3e appeared as best among them whereas 3-aryl analogues were found to be less active. According to the SAR analysis the order of effectiveness of heteroaryl moieties appeared as imidazol-5-yl > pyridin-2-yl > indol-5-yl > thiophen-2-yl > pyridin-3-yl > furan-3-yl. The in silico docking studies not only highlighted the key role of the carbonyl oxygen of isoindolin-1-one ring in interacting with SIRT1 via H-bond formation but also indicated important involvements of other hydrophobic interactions. Based on the in vitro and in silico studies the compound 3e emerged as an initial hit for further pharmacological evaluation.
Electrochemical synthesis of isobenzofuran-1-imines using oxidative halocyclization ofo-alkynylbenzamides
Anandhan, Ramasamy,Bhagavathiachari, Muthuraaman,Bhargava Reddy, Mandapati,Peri, Rajagopal
supporting information, p. 6792 - 6796 (2021/08/20)
Electrochemical oxidative 5-exo-dig-oxo-halocyclization ofo-alkynylbenzamides was achieved using readily available NaX (X = Cl, Br and I) salts under mild reaction conditions. The use of a cheap and highly stable sodium halide as a halide ion source is im
Phosphazene Superbase-Mediated Regio- and Stereoselective Iodoaminocyclization of 2-(1-Alkynyl)benzamides for the Synthesis of Isoindolin-1-ones
Mehta, Saurabh,Brahmchari, Dhirendra
, p. 5492 - 5503 (2019/05/10)
Phosphazene superbase P4-t-Bu mediated iodoaminocyclization of 2-(1-alkynyl)benzamides is reported. The reaction works under ambient conditions and instantaneously results in the synthesis of isoindolin-1-ones in 65-97% yields, in a regio- and stereoselective manner. The exclusive formation of products with Z-geometry (across the exo C?C bond) has been confirmed through X-ray crystallography. The methodology also provides an easy access to aristolactams, an important class of natural products. This has been successfully demonstrated by synthesizing two aristolactam derivatives (including Cepharanone B).
Regio- and Stereoselective Synthesis of Isoindolin-1-ones through BuLi-Mediated Iodoaminocyclization of 2-(1-Alkynyl)benzamides
Brahmchari, Dhirendra,Verma, Akhilesh K.,Mehta, Saurabh
supporting information, p. 3339 - 3347 (2018/03/23)
A simple and straightforward synthesis of isoindolin-1-ones is reported. Exclusive N-cyclization of the amide functional group, an ambident nucleophile, was accomplished for the cyclization of 2-(1-alkynyl)benzamides using n-BuLi-I2/ICl. The methodology works with the primary amide and affords the desired isoindolinones in yields of 38-94%. Interestingly, the isolated products exhibit a Z-stereochemistry across the C=C double bond. The reaction mechanism involving the formation of either a vinylic anion or an intimate ion pair intermediate is proposed.
Formation of benzo[c]thiophen-1-aminium iodide by the reaction of o-alkynylbenzothioamide with iodine
Matsumoto, Shoji,Takada, Daiki,Kageyama, Hirokazu,Akazome, Motohiro
supporting information, p. 1082 - 1085 (2014/02/14)
Reaction of o-alkynylbenzothioamide with molecular iodine was investigated. Unique benzo[c]thiophen-1-aminium iodide was obtained when the tertiary thioamide was used as a reactant. The reaction proceeded efficiently in less polar solvent, whereas the cor
Formation of benzo[c]thiophen-1-aminium iodide by the reaction of o-alkynylbenzothioamide with iodine
Matsumoto, Shoji,Takada, Daiki,Kageyama, Hirokazu,Akazome, Motohiro
supporting information, p. 1082 - 1085 (2015/02/19)
Reaction of o-alkynylbenzothioamide with molecular iodine was investigated. Unique benzo[c]thiophen-1-aminium iodide was obtained when the tertiary thioamide was used as a reactant. The reaction proceeded efficiently in less polar solvent, whereas the cor
Regio- and stereoselective synthesis of cyclic imidates via electrophilic cyclization of 2-(1-alkynyl)benzamides. A correction
Mehta, Saurabh,Yao, Tuanli,Larock, Richard C.
supporting information, p. 10938 - 10944 (2013/02/22)
The electrophilic cyclization of 2-(1-alkynyl)benzamides affords high yields of cyclic imidates, instead of the previously reported isoindolin-1-ones, where cyclization proceeds on the oxygen of the carbonyl group rather than the nitrogen of the amide fun
Regio- and stereoselective synthesis of isoindolin-1-ones via electrophilic cyclization
Yao, Tuanli,Larock, Richard C.
, p. 1432 - 1437 (2007/10/03)
(Chemical Equation Presented) A variety of substituted isoindolin-1-ones are readily prepared in good to excellent yields under very mild reaction conditions by the reaction of o-(1-alkynyl)benzamides with ICl, I2, and NBS. In a few cases, subs
