WIN 64821
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01635 |
| CAS | 150881-27-9 |
| Molecular Weight | 664.7 |
| Molecular Formula | C40H36N6O4 |
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Description
WIN 64821 is a nonpeptide antagonist of Neurokinin, which is isolated from Aspergillus sp. SC391.
Specification
| Synonyms | WIN-64821 |
| IUPAC Name | (1R,4S,7S,9R)-4-benzyl-9-[(1R,4S,7S,9R)-4-benzyl-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-trien-9-yl]-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-triene-3,6-dione |
| Canonical SMILES | C1C2C(=O)NC(C(=O)N2C3C1(C4=CC=CC=C4N3)C56CC7C(=O)NC(C(=O)N7C5NC8=CC=CC=C68)CC9=CC=CC=C9)CC1=CC=CC=C1 |
| InChI | InChI=1S/C40H36N6O4/c47-33-31-21-39(25-15-7-9-17-27(25)43-37(39)45(31)35(49)29(41-33)19-23-11-3-1-4-12-23)40-22-32-34(48)42-30(20-24-13-5-2-6-14-24)36(50)46(32)38(40)44-28-18-10-8-16-26(28)40/h1-18,29-32,37-38,43-44H,19-22H2,(H,41,47)(H,42,48)/t29-,30-,31-,32-,37+,38+,39-,40-/m0/s1 |
| InChI Key | ZEANERNKMXBETI-BJHDJDSNSA-N |
Properties
| Appearance | White Powder |
| Melting Point | 203-205°C |
Reference Reading
1. Copper-mediated dimerization to access 3a,3a'-bispyrrolidinoindoline: diastereoselective synthesis of (+)-WIN 64821 and (-)-ditryptophenaline
Kangjiang Liang, Xu Deng, Xiaogang Tong, Dashan Li, Ming Ding, Ankun Zhou, Chengfeng Xia Org Lett. 2015 Jan 16;17(2):206-9. doi: 10.1021/ol5032365. Epub 2015 Jan 7.
A copper-mediated cyclization and dimerization of tryptamine or tryptophan was developed to generate a C2-symmetry C3(sp(3))-C3(sp(3)) bridge with two contiguous stereogenic quaternary carbons in one step. Impressively, the ratio between exo and endo cyclization products varies when different protecting groups of Nb are utilized. This dimerization reaction could be conducted in gram scale. With this dimerization method, both endocyclotryptophan (+)-WIN 64821 and exocyclotryptophan (-)-ditryptophenaline were synthesized in 5 steps.
2. Stereodivergent Synthesis of Bispyrrolidinoindoline Alkaloidal Scaffolds and Generation of a Lead Candidate with Stereospecific Antiproliferative Activity
Mitsuhiro Wada, Hiroyuki Suzuki, Mitsuyasu Kato, Hideaki Oikawa, Akira Tsubouchi, Hiroki Oguri Chembiochem. 2019 May 15;20(10):1273-1281. doi: 10.1002/cbic.201800815. Epub 2019 Mar 28.
The fungal secondary metabolites (+)-WIN 64821 and (-)-ditryptophenaline are biosynthesized through condensation of l-tryptophan and l-phenylalanine, followed by reductive dimerization with generation of stereochemical variations. Inspired by the stereodivergent biogenetic process, we designed and synthesized a collection of bispyrrolidinoindoline diketopiperazine alkaloids and their analogues with systematic diversification of the stereochemistry of the privileged structural motif of the fungal alkaloids. Not only the stereochemical modifications of (+)-WIN 64821 at the 3-/3'-, 11-/11'-, and 15-/15'-positions, but also ring cleavage of the diketopiperazine moieties, allowed the generation of a lead compound exhibiting potent growth inhibitory activity (IC50 =3.03 μm) toward human colon cancer cells. Structure-activity relationship studies revealed that all six stereogenic centers were essential for the pharmacophore. High cell densities dramatically intensified the cytotoxic activities of the lead compound.
3. Exploration of a KI-catalyzed oxidation system for direct construction of bispyrrolidino[2,3-b]indolines and the total synthesis of (+)-WIN 64821
Si-Kai Chen, Ju-Song Yang, Kun-Long Dai, Fu-Min Zhang, Xiao-Ming Zhang, Yong-Qiang Tu Chem Commun (Camb). 2020 Jan 4;56(1):121-124. doi: 10.1039/c9cc08646c. Epub 2019 Dec 3.
A facile and environmentally benign KI(cat.)/NaBO3·4H2O oxidation system has been developed for the tandem oxidative aminocyclization/coupling of tryptamines, affording a series of 3a,3a'-bispyrrolidino[2,3-b]indolines with high efficiency (up to 94% yield). This reaction features an electrophilic "I+" mechanism, which is importantly quite different from and milder than the typical radical-involving process, and can be readily amplified for the total synthesis of (+)-WIN 64821.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
