1227263-77-5

Basic information

• Product Name: (3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol
• Synonyms: (3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol
• CAS NO: 1227263-77-5
• Molecular Weight: 192.261
• Mol File: 1227263-77-5.mol

Chemical Properties

• CAS DataBase Reference: (3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol(1227263-77-5)
• EPA Substance Registry System: (3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol(1227263-77-5)

Safety Data

• Hazardous Substances Data: 1227263-77-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(3S)-1-[(2-aminophenyl)methyl]pyrrolidin-3-ol is used as a potential pharmaceutical candidate for various applications due to its unique structure and functional groups. Its amine and alcohol groups may contribute to its biological activity, making it a candidate for development as a neurotransmitter or enzyme inhibitor, among other pharmacological functions.
Used in Research and Development:
In the field of scientific research, (3S)-1-[(2-aminophenyl)methyl]pyrrolidin-3-ol serves as a subject for further investigation to explore its specific properties and potential uses. This includes understanding its interactions with biological systems and assessing its efficacy and safety in various applications, which may ultimately lead to its integration into medical treatments or other industries.

Upstream product

• 6159-55-3 (+)-vasicinol 

Downstream Products

• 101385-90-4 (S)-N-benzyl-3-hydroxypyrrolidine 
• 486-64-6 (S)-3-hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one 
• 114636-29-2 (3S)-3-azido-1-(phenylmethyl)pyrrolidine 
• 116143-03-4 (3R)-3-azido-1-(phenylmethyl)pyrrolidine 

Relevant articles and documents

Synthesis of Ofornine mimics from natural product l-vasicine as anti-hypertensive agents

We report the chemical synthesis of Ofornine mimics from l-vasicine, structure-activity relationship studies and their in vivo screening for anti-hypertensive action in Wistar rats. It was observed that most of the analogs possessed anti-hypertensive effect; however, the duration of the effect was variable and mostly transient. The results demonstrated that the analogs 12, 13, 14, 15, and 16 showed a sharp and significant decrease in systolic and diastolic blood pressure for 30–60 min after intravenous administration. Analog (S)-(3-hydroxypyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone (8) showed a significant decrease in blood pressure in a dose dependent manner whose maximal response lowered to 79.29 ± 4.26 mmHg of SBP and 62.55 ± 2.9 of DBP at 10 mg/kg intravenous dose. Further, the significant anti-hypertensive effect of 8 lasted for about 2.5 h at 10 mg/kg dose. We also evaluated the acute toxicity of the analog 8 as per the OECD guidelines and the compound was found to be safe up to the dose of 2000 mg/kg body weight. These preclinical findings suggest that the analog 8 could be considered as a promising lead and a durable anti-hypertensive drug candidate and deserves further investigation. The SAR studies clearly showed that the amide, hydroxyl and pyridine ring plays important role in showing the activity.

Exploring Derivatives of Quinazoline Alkaloid l-Vasicine as Cap Groups in the Design and Biological Mechanistic Evaluation of Novel Antitumor Histone Deacetylase Inhibitors

l-Vasicine is a quinazoline alkaloid with an electron dense ring and additional functionalities in its structure. Employing target oriented synthesis (TOS) based on in silico studies, molecules with significant docking scores containing different derivatives of l-vasicine as caps were synthesized. Interestingly, one molecule, i.e., 4a, which contained 3-hyroxypyrrolidine as a cap group and a six carbon long aliphatic chain as a linker was found to inhibit HDACs. 4a showed more specificity toward class I HDAC isoforms. Also 4a was found to be less cytotoxic toward normal cell lines as compared to cancer cell lines. 4a inhibited cancer cell growth and induced cell death by various mechanisms. However, 4a was found to induce cell death independent of ROS generation, and unlike many natural product based HDAC inhibitors, 4a was found to be nontoxic under in vivo conditions. Importantly, we for the first time report the possibility of using a 3-hydroxypyrrolidine cap for the synthesis of HDAC inhibitors with good potency.

Natural (-)-vasicine as a novel source of optically pure 1-benzylpyrrolidin-3-ol

A facile and scalable methodology for the preparation of optically active (3S)-1-benzylpyrrolidin-3-ol (3), an important drug precursor, is reported. Starting from the naturally occurring alkaloid (-)-vasicine (1), a major alkaloid of the plant Adhatoda vasica, 3 was obtained in 84% overall yield (Scheme 3). Copyright

PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE N-BENZYL-3 HYDROXYPYRROLIDINES

The present invention relates to a facile, highly efficient and economical process for the preparation of optically active N-benzyl-3-hydroxypyrrolidine in high yield from a naturally occurring alkaloid vasicine. The natural alkaloid vasicine is used as a precursor of (S)—N-benzyl-3-hydroxypyrrolidine and (R)—N-benzyl-3-hydroxypyrrolidines which can easily be sourced from the medicinal plant Adatoda vasica by the method known in the art and transformed to optical isomers (R) and (S)—N-benzyl-3-hydroxypyrrolidine by the method described in the present invention.

A PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE N-BENZYL-3 HYDROXYPYRROLIDINES

The present invention relates to a facile, highly efficient and economical process for the preparation of optically active N-benzyl-3-hydroxypyrrolidine in high yield from a naturally occurring alkaloid vasicine. The natural alkaloid vasicine is used as a precursor of (S)-N-benzyl-3-hydroxypyrrolidine and (R)-N-benzyl-3-hydroxypyrrolidines which can easily be sourced from the medicinal plant Adatoda vasica by the method known in the art and transformed to optical isomers (R) and (S)-N-benzyl-3-hydroxypyrrolidine by the method described in the present invention.