1032754-93-0

Basic information

• Product Name: (S)-1-[4-[[2-(2-Aminopyrimidin-5-yl)-7-methyl-4-(morpholin-4-yl)thieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one
• Synonyms: (S)-1-[4-[[2-(2-Aminopyrimidin-5-yl)-7-methyl-4-(morpholin-4-yl)thieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one;GNE 390;GDC-0980;(S)-1-(4-((2-(2-aMinopyriMidin-5-yl)-7-Methyl-4-Morpholinothieno[3,2-d]pyriMidin-6-yl)Methyl)piperazin-1-yl)-2-hydroxypropan-1-one;GDC-0980 (RG7422);Apitolisib;Apitolisib (GDC-0980, RG7422);(S)-1-[4-[[2-(2-Aminopyrimidin-5-yl)-7-methyl-4-(morpholin-4-yl)thieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one GNE 390 GDC0980(RG7422)
• CAS NO: 1032754-93-0
• Molecular Formula: C₂₃H₃₀N₈O₃S
• Molecular Weight: 498.61
• Product Categories: An inhibitor of Class I PI3 kinase and mTOR kinase.;PI3K/Akt/mTOR;Inhibitors;Akt;mTOR;PI3K
• Mol File: 1032754-93-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 718.6±70.0 °C at 760 mmHg
• Flash Point: 388.4±35.7 °C
• Appearance: /
• Density: 1.399
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 13.90±0.20(Predicted)
• CAS DataBase Reference: (S)-1-[4-[[2-(2-Aminopyrimidin-5-yl)-7-methyl-4-(morpholin-4-yl)thieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-[4-[[2-(2-Aminopyrimidin-5-yl)-7-methyl-4-(morpholin-4-yl)thieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one(1032754-93-0)
• EPA Substance Registry System: (S)-1-[4-[[2-(2-Aminopyrimidin-5-yl)-7-methyl-4-(morpholin-4-yl)thieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one(1032754-93-0)

Safety Data

• Hazardous Substances Data: 1032754-93-0(Hazardous Substances Data)

Usage

Description

(S)-1-[4-[[2-(2-Aminopyrimidin-5-yl)-7-methyl-4-(morpholin-4-yl)thieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one is a complex organic compound with a unique molecular structure. It is characterized by its potential applications in various fields, particularly in the pharmaceutical industry, due to its specific chemical properties and interactions with biological systems.

Uses

Used in Pharmaceutical Industry:
(S)-1-[4-[[2-(2-Aminopyrimidin-5-yl)-7-methyl-4-(morpholin-4-yl)thieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one is used as a key intermediate in the synthesis of various pharmaceutical compounds, specifically those targeting cancer cells. Its unique molecular structure allows for the development of potent inhibitors that can effectively interfere with cancer cell growth and proliferation.
Used in Synthesis of PI3K Inhibitors:
In the field of cancer research and treatment, (S)-1-[4-[[2-(2-Aminopyrimidin-5-yl)-7-methyl-4-(morpholin-4-yl)thieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one is used as a crucial component in the synthesis of PI3K inhibitors. These inhibitors are designed to target and inhibit the PI3K/mTOR pathway, which plays a significant role in the growth and survival of various types of cancer cells. By inhibiting this pathway, the compound can potentially lead to the development of more effective treatments for carcinomas and other cancer types.
Used in Drug Delivery Systems:
Similar to gallotannin, (S)-1-[4-[[2-(2-Aminopyrimidin-5-yl)-7-methyl-4-(morpholin-4-yl)thieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one can also be incorporated into drug delivery systems to enhance its bioavailability, delivery, and therapeutic outcomes. By employing various organic and metallic nanoparticles as carriers, the compound can be more effectively transported to target cancer cells, improving its overall efficacy and potentially leading to better treatment outcomes for patients.

Biological Activity

gdc-0980 (rg7422) is a selective, novel, potent and orally bioavailable inhibitor of class 1 pi3k/mtor kinase with the ki value of 17nmol/l for mtor kinase [1].gdc-0980 (rg7422) has shown the effective inhibition with the ic50 values of ＜200nmol/l in prostate, breast and nsclc lines, respectinely. in addition, gdc-0980 (rg7422) has been reported to reduce cell viability in kpl4 cells by cell-cycle inhibition and induction of apoptosis with the ic50 value of 109nm and the ec50 value of 78nm. furthermore, gdc-0980 (rg7422) has been revealed to significantly inhibit tumor responses in xenograft models in oral dose of the compound. besides, gdc-0980 (rg7422) has been noted to enhance the antitumor activity in combination with antitumor agents ( docetaxel) in vivo [1].

references

[1] wallin jj1, edgar ka, guan j, berry m, prior ww, lee l, lesnick jd, lewis c, nonomiya j, pang j, salphati l, olivero ag, sutherlin dp, o'brien c, spoerke jm, patel s, lensun l, kassees r, ross l, lackner mr, sampath d, belvin m, friedman ls. gdc-0980 is a novel class i pi3k/mtor kinase inhibitor with robust activity in cancer models driven by the pi3k pathway. mol cancer ther. 2011 dec;10(12):2426-36. doi: 10.1158/1535-7163.mct-11-0446. epub 2011 oct 13.

InChI:InChI=1S/C23H30N8O3S/c1-14-17(13-29-3-5-31(6-4-29)22(33)15(2)32)35-19-18(14)27-20(16-11-25-23(24)26-12-16)28-21(19)30-7-9-34-10-8-30/h11-12,15,32H,3-10,13H2,1-2H3,(H2,24,25,26)/t15-/m0/s1

Upstream product

• 936250-22-5 (2-aminopyrimidin-5-yl)boronic acid 
• 1032757-58-6 (S)-1-(4-((2-chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)-2-hydroxypropan-1-one 
• 71-23-8 propan-1-ol 

Relevant articles and documents

A practical, protecting-group-free synthesis of a PI3K/mTOR inhibitor

We report a practical and protecting-group-free synthesis amenable to produce multikilogram amounts of PI3K/mTOR inhibitor GDC-0980. The route employed metalation/formylation and reductive amination followed by a metal catalyzed Suzuki-Miyaura cross-coupling. The metalation was performed via triarylmagnesiate intermediates allowing formylation under noncryogenic conditions. 2-Picoline·BH3 was employed to replace Na(OAc)3BH in the reductive amination and to eliminate the use of molecular sieves. A concise one-step synthesis was developed for the selective monoamidation of piperazine with (S)-lactate to produce the piperazine lactamide starting material. The boronic acid was produced from 2-amino-5-bromopyrimidine in a one-step and protecting-group-free approach. The final crystallization in 1-propanol and water afforded the API in 59% overall yield in four steps and >99% purity by HPLC.