53948-09-7Relevant academic research and scientific papers
ARISTOLACTAMS AND 4,5-DIOXOAPORPHINES FROM PIPER LONGUM
Desai, Sanjay J.,Prabhu, Bharathi R.,Mulchandani, Newand B.
, p. 1511 - 1516 (1988)
Nine alkaloids were isolated from the cold ethanol extract of Piper longum roots, of which six known compounds were identified as cepharadione B, cepharadione A, cepharanone B, aristolactam AII, norcepharadione B, and 2-hydroxy-1-methoxy-4H-dibenzoquinoline-4,5(6H)-dione.The three new alkaloids were characterized as 10-amino-4-hydroxy-3-methoxyphenanthrene-1-carboxylic acid lactam , 10-amino-4-hydroxy-2,3-dimethoxyphenanthrene-1-carboxylic acid lactam and 2-hydroxy-1-methoxy-6-methyl-4H-dibenzoquinoline-4,5(6H)-dione .Key Word Index - Piper longum; Piperaceae; root alkaloids; aristolactams; dioxoaporphines; piperolactam A; piperolactam B; piperadione; NMR.
A simple, efficient route to the synthesis of dibenzocoumaranones and aristolactams
Estevez,Carmen Villaverde,Estevez,Castedo
, p. 5145 - 5146 (1992)
We report the first synthesis of dibenzo[cdf]coumaranones that could be readily transformed into their nitrogen analogues, the aristolactams.
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).
Pd(II)/Cu(II)-Catalyzed Regio- and Stereoselective Synthesis of (E)-3-Arylmethyleneisoindolin-1-ones Using Air as the Terminal Oxidant
Youn, So Won,Ko, Tae Yun,Kim, Young Ho,Kim, Yun Ah
supporting information, p. 7869 - 7874 (2019/01/14)
Regio- and stereoselective synthesis of (E)-3-arylmethyleneisoindolin-1-ones via Pd(II)/Cu(II)-catalyzed one-pot C-C/C-N bond forming sequence between amides and styrenes is reported. This method provides facile and rapid access to a diverse range of such compounds using readily available starting materials under mild aerobic conditions with good functional group tolerance and high selectivity and efficiency. Further elaboration of the products obtained from this process enabled very short and efficient syntheses of aristolactam and indoloisoquinolinone alkaloids.
Total synthesis of aristolactam alkaloids: Via synergistic C-H bond activation and dehydro-Diels-Alder reactions
Reddy, Mallu Chenna,Jeganmohan, Masilamani
, p. 4130 - 4135 (2017/07/11)
A concise total synthesis of aristolactam alkaloids by a synergistic combination of C-H bond activation and dehydro-Diels-Alder reactions is described. To achieve the synthesis two new synthetic methodologies, namely the oxidative cyclization of benzamides with vinyl sulfone leading to 3-methyleneisoindolin-1-ones via a ruthenium-catalyzed C-H bond activation, and a dehydro-Diels-Alder reaction followed by the fluoride ion mediated desulfonylation of 3-methyleneisoindolin-1-ones with benzynes, were developed. The method presented allows the opportunity for the construction of all the rings of aristolactams from easily available starting materials.
Heteroannulation enabled by a bimetallic Rh(III)/Ag(i) relay catalysis: Application in the total synthesis of aristolactam BII
Ji, Wei-Wei,Lin,Li, Qingjiang,Wang, Honggen
supporting information, p. 5665 - 5668 (2017/07/07)
A redox-neutral bimetallic Rh(iii)/Ag(i) relay catalysis allowed the efficient construction of 3-alkylidene isoindolinones and 3-alkylidene isobenzofuranones. The Rh(iii) catalyst was responsible for the C-H monofluoroalkenylation reaction, whereas the Ag(i) salt was an activator for the follow-up cyclization. The methodology developed was applied as a key step in the rapid total synthesis of the natural product aristolactam BII.
Iodine/water-mediated oxidation of o-alkynylaroyl compounds and application of the products of oxidation in the synthesis of nitrogen heterocycles
Sakthivel, Karuppusamy,Srinivasan, Kannupal
, p. 3386 - 3396 (2013/06/27)
A facile iodine/water-mediated oxidation of the triple bond of o-alkynylaroyl compounds to furnish tricarbonyl compounds is reported. The reaction proceeds through the formation of isochromenol intermediates by the assistance of the neighbouring aroyl gro
Synthesis of aristolactam analogues and evaluation of their antitumor activity
Choi, Young Lok,Kim, Joa Kyum,Choi, Sang-Un,Min, Yong-Ki,Bae, Myung-Ae,Kim, Bum Tae,Heo, Jung-Nyoung
experimental part, p. 3036 - 3040 (2010/02/28)
A series of natural aristolactams and their analogues have been prepared and evaluated for antitumor activity against human cancer cells, including multi-drug resistant cell lines. Naturally occurring aristolactams, such as aristolactam BII (cepharanone B
PHENANTHRENE LACTAM DERIVATIVES HAVING ANTICANCER ACTIVITY AND METHOD FOR THE PREPARATION THEREOF
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Page/Page column 18, (2009/05/28)
The present invention relates to a phenanthrene lactam derivative having anticanter activity, a method for the preparation thereof, and a pharmaceutical composition comprising same.
Total synthesis of aristolactams via a one-pot Suzuki-Miyaura coupling/aldol condensation cascade reaction
Kim, Joa Kyum,Kim, Young Ha,Nam, Ho Tae,Kim, Bum Tae,Heo, Jung-Nyoung
supporting information; experimental part, p. 3543 - 3546 (2009/05/07)
(Chemical Equation Presented) A direct one-pot synthesis of phenanthrene lactams, which employs a Suzuki -Miyaura coupling/aldol condensation cascade reaction of isoindolin-1-one with 2-formylphenylboronic acid, has been developed. The approach is used to
