N²-(toluene-4-sulfonyl)-L-asparagine | 36212-66-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N²-(toluene-4-sulfonyl)-L-asparagine
• 英文别名: Nα-(4-methylbenzenesulfonyl)-L-asparagine；N-[(4-methylphenyl)sulfonyl]-L-asparagine；2-(S)-p-toluenesulfonylasparagine；Nα-tosylasparagine；(+)-p-toluenesulphonyl-L-asparagine；N²-(Toluol-4-sulfonyl)-L-asparagin；Tosyl-L-asparagine；(2S)-4-amino-2-[(4-methylphenyl)sulfonylamino]-4-oxobutanoic acid
• CAS: 36212-66-5
• 化学式: C₁₁H₁₄N₂O₅S
• mdl: MFCD01862367
• 分子量: 286.309
• InChiKey: VZCCSZRICJFBSI-VIFPVBQESA-N

物化性质

• 熔点：
  169-170°C dec.
• 沸点：
  583.6±60.0 °C(Predicted)
• 密度：
  1.419±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于二甲基亚砜，温水

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N²-(toluene-4-sulfonyl)-L-asparagine 在 sodium hydroxide 作用下， 生成
  参考文献：
  名称：

  Development of the Hofmann Rearrangement of Nα-Tosylasparagine through Calorimetric and NMR Analysis

  摘要：

  DOI：

  10.1021/jo980799l
• 作为产物：
  描述：

  L-天冬酰胺 生成 N²-(toluene-4-sulfonyl)-L-asparagine
  参考文献：
  名称：

  A novel synthesis of chiral guanidinium molecular hosts

  摘要：

  DOI：

  10.1016/0040-4039(90)80203-x

文献信息

• Syntheses and evaluation as antifolates of MTX analogs derived from 2,.omega.-diaminoalkanoic acids
  作者：J. R. Piper、G. S. McCaleb、J. A. Montgomery、F. A. Schmid、F. M. Sirotnak

  DOI：10.1021/jm00146a008

  日期：1985.8

  (MTX) analogues 27a-c bearing 2, omega-diaminoalkanoic acids (ornithine and its two lower homologues) in place of glutamic acid were synthesized by routes proceeding through N2-[4-(methylamino)benzoyl]-N omega-[(1,1-dimethylethoxy)carbonyl]-2, omega-diaminoalkanoic acid ethyl esters and N2-[4-(methylamino)benzoyl]-N5-[(1,1-dimethylethoxy)carbonyl]-2, 5-diaminopentanoic acid followed by alkylation with

  通过N2- [4-（甲基氨基）苯甲酰基]-N-ω-[[（+] []]合成带有2的ω-二氨基链烷酸（鸟氨酸及其两个较低的同系物）的甲氨蝶呤（MTX）类似物27a-c 1,1-二甲基乙氧基）羰基] -2，ω-二氨基链烷酸乙酯和N2- [4-（甲基氨基）苯甲酰基] -N5-[（1,1-二甲基乙氧基）羰基] -2，5-二氨基戊酸用6-（溴甲基）-2，4-吡啶二胺氢溴酸盐进行烷基化。27型类似物或适当前体的末端氨基上的反应导致其他MTX衍生物的侧链终止于脲基，甲基脲基，N-甲基-N-亚硝基脲基，N-（2-氯乙基）-N-亚硝基脲基和4-氯苯甲酰胺基。还制备了通过将异氰酸根合乙酸乙酯和2-异氰酸根合戊二酸二乙酯加入27a，b的乙基酯中而形成的不对称的二取代脲基。在这些脲基加合物（分别为32a，b和33a，b）中，只有33a成功水解为相应的纯酸，在这种情况下为三羧酸34（MTX代谢物MTX-γ-Glu的假
• [EN] HETEROCYCLIC COMPOUNDS THAT BLOCK THE EFFECTS OF ADVANCED GLYCATION END PRODUCTS (AGE)<br/>[FR] COMPOSES HETEROCYCLIQUES BLOQUANT LES EFFETS DES PRODUITS TERMINAUX AVANCES DE GLYCATION
  申请人：REDDYS LAB LTD DR

  公开号：WO2005040163A1

  公开（公告）日：2005-05-06

  The present invention relates to novel compounds of Formula (Ia) or (Ib), their pharmaceutically acceptable salts and pharmaceutically acceptable compositions containing them. Formula (Ia), or Formula (Ib) in the above formulae L represents Formula (I), Formula (II) or -(CH2)1- Q represents Formula (III), or Formula (IV). The present invention also relates to a process for the preparation of the above said novel compounds, their pharmaceutically acceptable salts and pharmaceutical compositions containing them. The present invention also relates to methods and compositions comprising compounds that treat pathophysiological conditions arising from inflammatory responses. In particular, the present invention is directed to compounds that inhibit or block glycated protein produced induction of the signaling-associated inflammatory responses in tissues, including endothelial cells. The present invention relates to compounds that inhibit smooth muscle proliferation. The present invention also relates to compounds that act as modulators of Perlecan activity and expression. In particular, the present invention is directed to compounds that inhibit smooth muscle cell proliferation by modulating heparan sulfate proteoglycans (HSPG) such as Perlecan. The present invention further relates to the use of compounds to treat vascular occlusive conditions characterized by smooth muscle proliferation such as stenosis, restenosis, neointimal hyperplasia, and atherosclerosis. The compounds of Formula (I) are also useful for the treatment and/or prevention of cancer. The types of cancers include melanoma, prostate, leukemia, lymphoma, non-small lung cancers, cancer of the central nervous system, breast, colon, ovarian or renal cancer.

  本发明涉及公式（Ia）或（Ib）的新化合物，它们的药学上可接受的盐以及含有它们的药学上可接受的组合物。在上述公式中，公式（Ia）或公式（Ib）中的L代表公式（I）、公式（II）或-(CH2)1-，Q代表公式（III）或公式（IV）。本发明还涉及制备上述新化合物、其药学上可接受的盐和含有它们的药物组合物的方法。本发明还涉及包括治疗由炎症反应引起的病理生理条件的化合物的方法和组合物。具体而言，本发明涉及抑制或阻断组织中糖化蛋白诱导的与信号相关的炎症反应的化合物。本发明涉及抑制平滑肌增殖的化合物。本发明还涉及作为Perlecan活性和表达调节剂的化合物。具体而言，本发明涉及通过调节肝素硫酸蛋白聚糖（HSPG）如Perlecan来抑制平滑肌细胞增殖的化合物。本发明进一步涉及利用化合物治疗由平滑肌增殖特征的血管闭塞性疾病，如狭窄、再狭窄、新内膜增生和动脉粥样硬化。公式（I）的化合物也可用于治疗和/或预防癌症。癌症类型包括黑色素瘤、前列腺癌、白血病、淋巴瘤、非小细胞肺癌、中枢神经系统癌症、乳腺癌、结肠癌、卵巢癌或肾癌。
• Analogs of the cytostatic cyclic tetrapeptide chlamydocin. Synthesis of N.beta.-(N-maleoylglycyl) and N.beta.-(tert-butyloxycarbonyl) derivatives of cyclo(Gly-L-Phe-D-Pro-L-Dap)
  作者：Daniel H. Rich、Ronald D. Jasensky、Gerald C. Mueller、Kristin E. Anderson

  DOI：10.1021/jm00137a017

  日期：1981.5

  The synthesis of analogues of the cytostatic cyclic tetrapeptide chlamydocin is described. cyclo(Gly-L-Phe-D-Pro-N beta-Boc-L-Dap) (4) was prepared from N beta-(tert-butyloxycarbonyl)-L-diaminopropionic acid methyl ester (Dap) and Cbz-Gly-L-Phe-D-Pro using DCC/HOBt as the coupling reagent. The methyl ester was saponified to the acid, which was converted to the 2,4,5-trichlorophenyl (Tcp) ester by reaction

  描述了细胞生长抑制性环四肽衣原蛋白的类似物的合成。环（Gly-L-Phe-D-Pro-Nβ-Boc-L-Dap）（4）由Nβ-（叔丁氧羰基）-L-二氨基丙酸甲酯（Dap）和Cbz-Gly-使用DCC / HOBt作为偶联剂的L-Phe-D-Pro。将甲酯皂化为酸，通过与三氯苯酚和DCC反应将其转化为2,4,5-三氯苯基（Tcp）酯。通过氢解除去N-（苄氧羰基）基团，并且使胺活性酯在95℃下在吡啶中环化。分离出Boc保护的环状四肽4，产率为14％。将环四肽4转化为环[[Gly-L-Phe-D-Pro-Nβ-（N-马来酰甘氨酰基）-L-Dap]]（5），以测试衣原蛋白受体上可能存在的巯基。去除叔丁氧羰基，然后与N-马来酰甘氨酸和DCC / HOBt在二氯甲烷中反应，以68％的产率得到环状四肽5。马来酰基环状四肽5不会抑制[3H]胸腺嘧啶核苷掺入小牛胸腺淋巴细胞中，其浓度比衣原霉素（6 nM）的IC50高1000倍。
• Synthesis, Characterization, and Reactivity of an Ethynyl Benziodoxolone (EBX)–Acetonitrile Complex
  作者：Masaharu Yudasaka、Daisuke Shimbo、Toshifumi Maruyama、Norihiro Tada、Akichika Itoh

  DOI：10.1021/acs.orglett.9b00005

  日期：2019.2.15

  The synthesis of a crystalline ethynyl-1,2-benziodoxol-3(1H)-one (EBX)–acetonitrile complex is described. EBX has been widely used as an active species for a variety of reactions; however, its high instability has so far prevented its isolation. The EBX–acetonitrile is self-assembled into a double-layered honeycomb structure through weak hypervalent iodine secondary interactions and hydrogen bonding

  描述了结晶的乙炔基1,2-苯并恶恶唑-3（1 H）-一（EBX）-乙腈配合物的合成。EBX已被广泛用作各种反应的活性物种。但是，到目前为止，它的高度不稳定性阻止了它的隔离。EBX-乙腈通过弱的高价碘二次相互作用和氢键自组装成双层蜂窝结构。所述Ñ -ethynylation各种使用EBX -乙腈络合物作为在温和条件下的衬底还描述磺胺类药物。
• HIV protease inhibitors based on amino acid derivatives
  申请人：——

  公开号：US20020151546A1

  公开（公告）日：2002-10-17

  A compound selected from the group consisting of a compound of formula I 1 a compound of formula II 2 and when the compound of formula I and II comprises an amino group pharmaceutically acceptable ammonium salts thereof, wherein R 1 , R 2 , Cx, n, R 3 , R 4 , R 5 , Y are as defined in the specification.

  从以下组中选择的化合物，其中化合物I的化合物，化合物II的化合物，以及当化合物I和II的化合物包括其氨基团的药用可接受铵盐，其中R1、R2、Cx、n、R3、R4、R5、Y的定义如规范中所述。