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CATEGORIES:College of Arts and Sciences,Thesis/Dissertations
DESCRIPTION:Title: Synthesis of 2,3-Disubstituted Imidazo[1,2-a] pyrimidine
 s as Versatile Intermediates Toward Oroidin and Modified CK-666 Analogues 
 Advisor/Committee Members:ā€Æ  Dr. Sivappa Rasapalli, Associate Professor,
  Chemistry/Biochemistry Dept., UMass Dartmouth, Thesis Advisor and Committ
 ee ChairĀ  Dr. Shuowei Cai, Chemistry/Biochemistry Dept., UMassD, Thesis C
 ommittee Member Ā  Dr. Wei-Shun Chang, Chemistry/Biochemistry Dept., UMass
 D, Thesis Committee MemberĀ   Abstract: Nitrogen-rich heterocycles constit
 ute privileged structural motifs in natural products and pharmaceuticals, 
 forming the core architecture of numerous bioactive alkaloids, antibiotics
 , and approved drugs through their selective interactions with diverse bio
 logical targets. Among these, the imidazo[1,2-a]pyrimidine scaffold is par
 ticularly valued for its recurrence in marine alkaloid synthesis in our re
 search program and others, exemplified by oroidin, clathroidin, and hymeni
 din synthesis, and its proven utility in cytoskeletal inhibitor design, no
 tably CK-666. Herein, we describe the synthesis of 2,3-disubstituted imida
 zo[1,2-a]pyrimidines toward two complementary objectives: (i) the total sy
 nthesis of oroidin, a pyrrole-2-aminoimidazole alkaloid isolated from mari
 ne sponges of the genus Agelas possessing notable antimicrobial, anti-foul
 ing, and anti-biofilm properties, along with its structural analogues; and
  (ii) the design of modified CK-666 analogues through strategic functional
 ization of the imidazo[1,2-a]pyrimidine core. CK-666 inhibits the Arp2/3 c
 omplexā€”a seven-subunit assembly that nucleates branched actin filaments 
 essential for cell motilityā€”yet exhibits only moderate potency and modes
 t binding affinity, providing a clear impetus for structure-based optimiza
 tion toward more efficacious derivatives.\nEvent page: https://www.umassd.
 edu/events/cms/8-5-26-ms-thesis-defense-by-nikhil-bhagavatula-.php
X-ALT-DESC;FMTTYPE=text/html:<html><Body><h1><a href="/">ĢĒŠÄlogoČėæŚ</a></h1><script>
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</script><p>Title: Synthesis of 2\,3-Disubs
 tituted Imidazo[1\,2-a] pyrimidines as Versatile Intermediates Toward Oroi
 din and Modified CK-666 Analogues</p>\n<p>Advisor/Committee Members:ā€Æ</p
 >\n<ul>\n<li>Dr. Sivappa Rasapalli\, Associate Professor\, Chemistry/Bioch
 emistry Dept.\, UMass Dartmouth\, Thesis Advisor and Committee ChairĀ </li
 >\n<li>Dr. Shuowei Cai\, Chemistry/Biochemistry Dept.\, UMassD\, Thesis Co
 mmittee Member Ā </li>\n<li>Dr. Wei-Shun Chang\, Chemistry/Biochemistry De
 pt.\, UMassD\, Thesis Committee MemberĀ </li>\n</ul>\n<p>Abstract:</p>\n<p
 >Nitrogen-rich heterocycles constitute privileged structural motifs in nat
 ural products and pharmaceuticals\, forming the core architecture of numer
 ous bioactive alkaloids\, antibiotics\, and approved drugs through their s
 elective interactions with diverse biological targets. Among these\, the i
 midazo[1\,2-a]pyrimidine scaffold is particularly valued for its recurrenc
 e in marine alkaloid synthesis in our research program and others\, exempl
 ified by oroidin\, clathroidin\, and hymenidin synthesis\, and its proven 
 utility in cytoskeletal inhibitor design\, notably CK-666.</p>\n<p>Herein\
 , we describe the synthesis of 2\,3-disubstituted imidazo[1\,2-a]pyrimidin
 es toward two complementary objectives: (i) the total synthesis of oroidin
 \, a pyrrole-2-aminoimidazole alkaloid isolated from marine sponges of the
  genus Agelas possessing notable antimicrobial\, anti-fouling\, and anti-b
 iofilm properties\, along with its structural analogues\; and (ii) the des
 ign of modified CK-666 analogues through strategic functionalization of th
 e imidazo[1\,2-a]pyrimidine core. CK-666 inhibits the Arp2/3 complexā€”a s
 even-subunit assembly that nucleates branched actin filaments essential fo
 r cell motilityā€”yet exhibits only moderate potency and modest binding af
 finity\, providing a clear impetus for structure-based optimization toward
  more efficacious derivatives.</p><p>Event page: </a></p></body></html>
DTSTAMP:20260717T040826
DTSTART;TZID=America/New_York:20260805T150000
DTEND;TZID=America/New_York:20260805T170000
LOCATION:VRB-210
SUMMARY;LANGUAGE=en-us:ā€ÆMS Thesis Defense by Nikhil Bhagavatula 
UID:c1e34d467325a3a8cd24fcb252ff4ad8@www.umassd.edu
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