184877-64-3

Basic information

• Product Name: madindoline A
• Synonyms: madindoline A
• CAS NO: 184877-64-3
• Molecular Formula: C₂₂H₂₇NO₄
• Molecular Weight: 369.45408
• Mol File: 184877-64-3.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: madindoline A(CAS DataBase Reference)
• NIST Chemistry Reference: madindoline A(184877-64-3)
• EPA Substance Registry System: madindoline A(184877-64-3)

Safety Data

• Hazardous Substances Data: 184877-64-3(Hazardous Substances Data)

Upstream product

• 303128-54-3 acetic acid 2-[3a-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,8a-tetrahydro-furo[2,3-b]indol-8-ylmethyl]-1-ethyl-3,4-dihydroxy-2-methyl-octyl ester 
• 302812-70-0 Acetic acid (E)-(R)-2-[(3aR,8aS)-3a-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,8a-tetrahydro-furo[2,3-b]indol-8-ylmethyl]-1-ethyl-2-methyl-oct-3-enyl ester 
• 302812-72-2 4-[3a-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,8a-tetrahydro-furo[2,3-b]indol-8-ylmethyl]-4-methyl-decane-3,5,6-trione 
• 303007-06-9 4-[3a-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,8a-tetrahydro-furo[2,3-b]indol-8-ylmethyl]-4-methyl-decane-3,5,6-triol 
• 302812-66-4 Acetic acid (E)-(R)-2-[(3aR,8aS)-3a-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,8a-tetrahydro-furo[2,3-b]indol-8-ylmethyl]-2-methyl-oct-3-enyl ester 
• 391612-39-8 (E)-(R)-2-[(3aR,8aS)-3a-(tert-Butyl-dimethyl-silanyloxy)-2,3,3a,8a-tetrahydro-furo[2,3-b]indol-8-ylmethyl]-2-methyl-oct-3-en-1-ol 
• 302812-68-6 (E)-(R)-2-[(3aR,8aS)-3a-(tert-Butyl-dimethyl-silanyloxy)-2,3,3a,8a-tetrahydro-furo[2,3-b]indol-8-ylmethyl]-2-methyl-oct-3-enal 
• 302812-60-8 (E)-(S)-2-Benzyloxymethyl-2-methyl-oct-3-enal 
• 302812-64-2 Acetic acid (E)-(S)-2-formyl-2-methyl-oct-3-enyl ester 
• 861642-07-1 (Z)-2-ethylidene-3-trimethylsilylhexanoyl chloride 
• 405297-80-5 [(2S),3aR,8aS]-3a-(tert-butyldimethylsilyloxy)-8-(2-methyl-3-trimethylacetoxypropyl)-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]indole 
• 405297-81-6 [(2S),3aR,8aS]-3a-(tert-butyldimethylsilyloxy)-8-(2-carboxypropyl)-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]indole 
• 444197-87-9 3-[3a-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,8a-tetrahydro-furo[2,3-b]indol-8-yl]-2-methyl-propan-1-ol 
• 405297-73-6 [(2S),3aR,8aS]-3a-(tert-butyldimethylsilyloxy)-8-(2-methoxycarbonylpropyl)-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]indole 

Relevant articles and documents

Total synthesis of madindoline A

The total synthesis of madindoline A was achieved. The key step of the synthesis is a reductive coupling of an acid-sensitive hydroxyfuroindoline derivative and a sterically hindered aldehyde using Sn(OTf)2-NaBH(OAc)3. After the redu

Synthetic applications of a three-component Mannich reaction. Total synthesis of IL-6 inhibitor (+)-madindoline A and B

A three-component Mannich reaction of 3a-hydroxyfuroindoline (3), β-ketoester and formaldehyde was employed as an efficient and concise method to synthesize naturally-occurring (+)-Madindolines A (1) and B (2). The scope and limitations of the Mannich rea

Design, synthesis, and biological activities of madindoline analogues

A research program is under way to develop a series of madindoline-based inhibitors targeting interleukin 6. Such inhibitors will have potential use in fighting a variety of diseases for which no effective therapeutic drugs currently exist. Madindoline is