Synthesis and Properties of a New Type of Terpyridine Cholesterol Derivative Gelator with Applications to Medical Treatments

<table class="table-group" id="tab4"><tr><td><table class="table"><tr><td class="thead-hr" colspan="5"><hr/></td></tr><tr class="thead"><td class="align_left"></td><td class="align_center">C</td><td class="align_center">H</td><td class="align_center">N</td><td class="align_center">O</td></tr><tr><td class="thead-hr" colspan="5"><hr/></td></tr><tr><td class="align_left">Theoretical value</td><td class="align_center">67.68</td><td class="align_center">5.68</td><td class="align_center">14.35</td><td class="align_center">12.29</td></tr><tr><td class="align_left">Actual value</td><td class="align_center">67.30</td><td class="align_center">5.20</td><td class="align_center">13.99</td><td class="align_center">12.32</td></tr><tr class="table-tr"><td colspan="5"><hr class="tbody-hr"/></td></tr></table></td></tr><tr class="table-fn"><td><div><sup>1</sup>H NMR (400 MHz, DMSO-<i>d</i><sub>6</sub>) <i>δ</i> 1.25–1.43 (m, 2H), 1.46–1.69 (dq, <span class="nowrap"><svg height="10.5647pt" id="M95" style="vertical-align:-1.928801pt" version="1.1" viewbox="-0.0498162 -8.6359 42.6863 10.5647" width="42.6863pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M429 650H175L169 622C251 614 259 612 244 532L174 152C163 91 152 37 135 -6C109 -72 67 -101 23 -113L33 -144C45 -143 73 -134 102 -119C186 -76 229 -1 254 133L327 532C341 609 347 613 423 622L429 650Z"></path></g><g transform="matrix(.013,0,0,-0.013,9.511,0)"><path d="M535 323V373H52V323H535ZM535 138V188H52V138H535Z"></path></g><g transform="matrix(.013,0,0,-0.013,20.774,0)"><path d="M384 0V27C293 34 287 42 287 114V635C232 613 172 594 109 583V559L157 557C201 555 205 550 205 499V114C205 42 199 34 109 27V0H384Z"></path></g><g transform="matrix(.013,0,0,-0.013,27.014,0)"><path d="M456 178V225H360V632H320C217 496 115 347 20 206V178H280V106C280 40 276 34 189 27V0H445V27C364 34 360 39 360 106V178H456ZM280 225H82C149 335 214 431 278 520H280V225Z"></path></g><g transform="matrix(.013,0,0,-0.013,33.254,0)"><path d="M113 -12C146 -12 170 11 170 46C170 78 146 103 114 103S58 78 58 46C58 11 82 -12 113 -12Z"></path></g><g transform="matrix(.013,0,0,-0.013,36.218,0)"><path d="M153 550H386L412 615L406 623H120L82 318C104 327 142 338 184 338C294 338 347 275 347 187C347 112 305 39 221 39C160 39 119 71 97 89C88 97 80 96 71 90C59 80 50 67 49 57C48 45 52 36 66 23C80 9 123 -12 169 -12C221 -11 288 15 342 59C403 109 431 165 431 225C431 308 366 395 238 395C212 395 165 379 127 364L153 550Z"></path></g></svg>,</span> 7.1 Hz, 4H), 2.14–2.30 (t, <span class="nowrap"><svg height="10.5647pt" id="M96" style="vertical-align:-1.928801pt" version="1.1" viewbox="-0.0498162 -8.6359 53.9435 10.5647" width="53.9435pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M429 650H175L169 622C251 614 259 612 244 532L174 152C163 91 152 37 135 -6C109 -72 67 -101 23 -113L33 -144C45 -143 73 -134 102 -119C186 -76 229 -1 254 133L327 532C341 609 347 613 423 622L429 650Z"></path></g><g transform="matrix(.013,0,0,-0.013,9.511,0)"><path d="M535 323V373H52V323H535ZM535 138V188H52V138H535Z"></path></g><g transform="matrix(.013,0,0,-0.013,20.774,0)"><path d="M447 623H65C61 580 56 530 47 475H76C100 541 106 550 172 550H388C308 376 196 170 91 -1L98 -12L172 -2C268 204 360 408 455 611L447 623Z"></path></g><g transform="matrix(.013,0,0,-0.013,27.016,0)"><path d="M113 -12C146 -12 170 11 170 46C170 78 146 103 114 103S58 78 58 46C58 11 82 -12 113 -12Z"></path></g><g transform="matrix(.013,0,0,-0.013,29.98,0)"><path d="M285 378C315 398 338 416 353 432C373 451 384 474 384 503C384 579 325 635 236 635H235C182 635 136 610 108 579L65 516L85 496C110 533 150 575 205 575C258 575 300 543 300 481C300 407 232 369 141 339L147 310C163 315 188 321 211 321C268 321 338 284 338 192C338 94 288 40 217 40C160 40 119 68 93 91C85 98 77 97 69 91C60 84 47 71 46 58C44 46 48 35 62 22C75 10 116 -12 162 -12C234 -12 424 62 424 224C424 297 373 359 285 376V378Z"></path></g><g transform="matrix(.013,0,0,-0.013,38.396,0)"><path d="M729 650H468V622C546 615 554 610 554 527V365H213V527C213 610 221 616 297 622V650H38V622C120 616 128 611 128 527V123C128 39 120 34 40 28V0H303V28C221 34 213 40 213 123V322H554V123C554 39 546 34 460 28V0H728V28C647 34 639 39 639 123V527C639 610 647 615 729 622V650Z"></path></g><g transform="matrix(.013,0,0,-0.013,48.223,0)"><path d="M387 138L374 114C336 54 316 33 240 33H141C223 167 303 295 385 423L379 437H149C112 437 100 443 94 458H73C65 415 50 352 39 314L64 305L78 332C106 388 119 403 191 403C214 403 246 403 280 403C198 270 117 142 31 15L38 0H367C382 40 399 86 413 125L387 138Z"></path></g></svg>,</span> 2H), 7.48–7.58 (dd, <span class="nowrap"><svg height="10.5647pt" id="M97" style="vertical-align:-1.928801pt" version="1.1" viewbox="-0.0498162 -8.6359 36.4229 10.5647" width="36.4229pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M429 650H175L169 622C251 614 259 612 244 532L174 152C163 91 152 37 135 -6C109 -72 67 -101 23 -113L33 -144C45 -143 73 -134 102 -119C186 -76 229 -1 254 133L327 532C341 609 347 613 423 622L429 650Z"></path></g><g transform="matrix(.013,0,0,-0.013,9.511,0)"><path d="M535 323V373H52V323H535ZM535 138V188H52V138H535Z"></path></g><g transform="matrix(.013,0,0,-0.013,20.774,0)"><path d="M447 623H65C61 580 56 530 47 475H76C100 541 106 550 172 550H388C308 376 196 170 91 -1L98 -12L172 -2C268 204 360 408 455 611L447 623Z"></path></g><g transform="matrix(.013,0,0,-0.013,27.016,0)"><path d="M113 -12C146 -12 170 11 170 46C170 78 146 103 114 103S58 78 58 46C58 11 82 -12 113 -12Z"></path></g><g transform="matrix(.013,0,0,-0.013,29.98,0)"><path d="M153 550H386L412 615L406 623H120L82 318C104 327 142 338 184 338C294 338 347 275 347 187C347 112 305 39 221 39C160 39 119 71 97 89C88 97 80 96 71 90C59 80 50 67 49 57C48 45 52 36 66 23C80 9 123 -12 169 -12C221 -11 288 15 342 59C403 109 431 165 431 225C431 308 366 395 238 395C212 395 165 379 127 364L153 550Z"></path></g></svg>,</span> 4.9 Hz, 2H), 7.98–8.09 (dt, <span class="nowrap"><svg height="10.5647pt" id="M98" style="vertical-align:-1.928801pt" version="1.1" viewbox="-0.0498162 -8.6359 36.4229 10.5647" width="36.4229pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M429 650H175L169 622C251 614 259 612 244 532L174 152C163 91 152 37 135 -6C109 -72 67 -101 23 -113L33 -144C45 -143 73 -134 102 -119C186 -76 229 -1 254 133L327 532C341 609 347 613 423 622L429 650Z"></path></g><g transform="matrix(.013,0,0,-0.013,9.511,0)"><path d="M535 323V373H52V323H535ZM535 138V188H52V138H535Z"></path></g><g transform="matrix(.013,0,0,-0.013,20.774,0)"><path d="M447 623H65C61 580 56 530 47 475H76C100 541 106 550 172 550H388C308 376 196 170 91 -1L98 -12L172 -2C268 204 360 408 455 611L447 623Z"></path></g><g transform="matrix(.013,0,0,-0.013,27.016,0)"><path d="M113 -12C146 -12 170 11 170 46C170 78 146 103 114 103S58 78 58 46C58 11 82 -12 113 -12Z"></path></g><g transform="matrix(.013,0,0,-0.013,29.98,0)"><path d="M244 635C114 635 38 519 38 422C38 317 111 240 217 240C236 240 255 244 277 256L345 292C311 140 203 39 59 15L64 -15C89 -15 150 -5 204 17C339 72 440 202 440 386C440 521 368 635 244 635ZM228 602C326 602 352 479 352 390C352 370 351 347 348 324C327 308 293 296 258 296C174 296 124 369 124 458C124 517 152 602 228 602Z"></path></g></svg>,</span> 4.0 Hz, 2H), 8.61–8.67 (d, <span class="nowrap"><svg height="10.5647pt" id="M99" style="vertical-align:-1.928801pt" version="1.1" viewbox="-0.0498162 -8.6359 53.9435 10.5647" width="53.9435pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M429 650H175L169 622C251 614 259 612 244 532L174 152C163 91 152 37 135 -6C109 -72 67 -101 23 -113L33 -144C45 -143 73 -134 102 -119C186 -76 229 -1 254 133L327 532C341 609 347 613 423 622L429 650Z"></path></g><g transform="matrix(.013,0,0,-0.013,9.511,0)"><path d="M535 323V373H52V323H535ZM535 138V188H52V138H535Z"></path></g><g transform="matrix(.013,0,0,-0.013,20.774,0)"><path d="M249 635C141 635 70 555 70 471C70 401 114 353 179 316C143 294 106 267 90 252C68 231 45 202 45 157C45 50 130 -12 237 -12C322 -12 435 52 435 169C435 256 372 304 303 343C349 374 375 398 383 407C401 429 411 458 411 487C411 569 344 635 249 635ZM238 603C285 603 337 567 337 482C337 422 310 385 276 358C205 393 145 426 145 500C145 552 179 603 238 603ZM248 20C183 20 125 70 125 163C125 218 158 268 206 300C284 261 355 217 355 143C355 66 308 20 248 20Z"></path></g><g transform="matrix(.013,0,0,-0.013,27.014,0)"><path d="M113 -12C146 -12 170 11 170 46C170 78 146 103 114 103S58 78 58 46C58 11 82 -12 113 -12Z"></path></g><g transform="matrix(.013,0,0,-0.013,29.978,0)"><path d="M241 635C89 635 35 457 35 312C35 153 89 -12 240 -12C390 -12 443 166 443 312C443 466 390 635 241 635ZM238 602C329 602 354 454 354 312C354 172 330 22 240 22C152 22 124 173 124 313S148 602 238 602Z"></path></g><g transform="matrix(.013,0,0,-0.013,38.393,0)"><path d="M729 650H468V622C546 615 554 610 554 527V365H213V527C213 610 221 616 297 622V650H38V622C120 616 128 611 128 527V123C128 39 120 34 40 28V0H303V28C221 34 213 40 213 123V322H554V123C554 39 546 34 460 28V0H728V28C647 34 639 39 639 123V527C639 610 647 615 729 622V650Z"></path></g><g transform="matrix(.013,0,0,-0.013,48.221,0)"><path d="M387 138L374 114C336 54 316 33 240 33H141C223 167 303 295 385 423L379 437H149C112 437 100 443 94 458H73C65 415 50 352 39 314L64 305L78 332C106 388 119 403 191 403C214 403 246 403 280 403C198 270 117 142 31 15L38 0H367C382 40 399 86 413 125L387 138Z"></path></g></svg>,</span> 2H), 8.73–8.79 (d, <span class="nowrap"><svg height="10.5647pt" id="M100" style="vertical-align:-1.928801pt" version="1.1" viewbox="-0.0498162 -8.6359 53.9435 10.5647" width="53.9435pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M429 650H175L169 622C251 614 259 612 244 532L174 152C163 91 152 37 135 -6C109 -72 67 -101 23 -113L33 -144C45 -143 73 -134 102 -119C186 -76 229 -1 254 133L327 532C341 609 347 613 423 622L429 650Z"></path></g><g transform="matrix(.013,0,0,-0.013,9.511,0)"><path d="M535 323V373H52V323H535ZM535 138V188H52V138H535Z"></path></g><g transform="matrix(.013,0,0,-0.013,20.774,0)"><path d="M456 178V225H360V632H320C217 496 115 347 20 206V178H280V106C280 40 276 34 189 27V0H445V27C364 34 360 39 360 106V178H456ZM280 225H82C149 335 214 431 278 520H280V225Z"></path></g><g transform="matrix(.013,0,0,-0.013,27.014,0)"><path d="M113 -12C146 -12 170 11 170 46C170 78 146 103 114 103S58 78 58 46C58 11 82 -12 113 -12Z"></path></g><g transform="matrix(.013,0,0,-0.013,29.978,0)"><path d="M447 623H65C61 580 56 530 47 475H76C100 541 106 550 172 550H388C308 376 196 170 91 -1L98 -12L172 -2C268 204 360 408 455 611L447 623Z"></path></g><g transform="matrix(.013,0,0,-0.013,38.396,0)"><path d="M729 650H468V622C546 615 554 610 554 527V365H213V527C213 610 221 616 297 622V650H38V622C120 616 128 611 128 527V123C128 39 120 34 40 28V0H303V28C221 34 213 40 213 123V322H554V123C554 39 546 34 460 28V0H728V28C647 34 639 39 639 123V527C639 610 647 615 729 622V650Z"></path></g><g transform="matrix(.013,0,0,-0.013,48.223,0)"><path d="M387 138L374 114C336 54 316 33 240 33H141C223 167 303 295 385 423L379 437H149C112 437 100 443 94 458H73C65 415 50 352 39 314L64 305L78 332C106 388 119 403 191 403C214 403 246 403 280 403C198 270 117 142 31 15L38 0H367C382 40 399 86 413 125L387 138Z"></path></g></svg>,</span> 2H), 8.79–8.84 (s, 2H), 9.00–9.11 (s, 1H), and 11.77–12.09 (s, 1H).<br/></div></td></tr></table>

<div>Elemental composition of 6-(2,2<span class="nowrap"><svg height="11.4859pt" id="M92" style="vertical-align:-0.04979992pt" version="1.1" viewbox="-0.0498162 -11.4361 3.89517 11.4859" width="3.89517pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.0091,0,0,-0.0091,0,-5.741)"><path d="M310 541L304 571C290 586 211 619 185 610L80 76L131 52L310 541Z"></path></g></svg>:</span>6<span class="nowrap"><svg height="11.4859pt" id="M93" style="vertical-align:-0.04979992pt" version="1.1" viewbox="-0.0498162 -11.4361 3.89517 11.4859" width="3.89517pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.0091,0,0,-0.0091,0,-5.741)"><path d="M310 541L304 571C290 586 211 619 185 610L80 76L131 52L310 541Z"></path></g></svg>,</span>2″-terpyridine-4<span class="nowrap"><svg height="11.4859pt" id="M94" style="vertical-align:-0.04979992pt" version="1.1" viewbox="-0.0498162 -11.4361 3.89517 11.4859" width="3.89517pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.0091,0,0,-0.0091,0,-5.741)"><path d="M310 541L304 571C290 586 211 619 185 610L80 76L131 52L310 541Z"></path></g></svg>-</span>formamide) hexanoic acid.</div>

International Journal of Polymer Science

tab4

Table 4

Table 4: Synthesis and Properties of a New Type of Terpyridine Cholesterol Derivative Gelator with Applications to Medical Treatments 