succinimidyl {(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propyl}carbamate | 270575-71-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: succinimidyl {(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propyl}carbamate
• 英文别名: 9H-fluoren-9-ylmethyl N-[(2S)-1-[(2,5-dioxopyrrolidin-1-yl)oxycarbonylamino]propan-2-yl]carbamate
• CAS: 270575-71-8
• 化学式: C₂₃H₂₃N₃O₆
• 分子量: 437.452
• InChiKey: SYFPIMKKBARYPR-AWEZNQCLSA-N

物化性质

• 熔点：
  161-163 °C
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  succinimidyl {(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propyl}carbamate 、 succinimidyl {(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-phenylpropyl}carbamate 生成 1-[(2S)-2-amino-3-phenylpropyl]-3-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-(carbamoylamino)propan-2-yl]carbamoylamino]-3-phenylpropan-2-yl]carbamoylamino]propan-2-yl]carbamoylamino]-3-phenylpropan-2-yl]carbamoylamino]propan-2-yl]urea
  参考文献：
  名称：

  O-琥珀酰亚胺基-（9 H-芴-9-甲氧基羰基氨基）乙基氨基甲酸酯衍生物为活化单体的固相合成低聚尿素

  摘要：

  描述了使用O-琥珀酰亚胺基- （9 H-芴-9-基甲氧基羰基氨基）乙基氨基甲酸酯衍生物作为活化单体在固相载体上高效逐步合成寡聚脲（直至九聚体）的方法。这些构建块被容易地制备，起始自Ñ -Fmoc保护的β 3 -氨基酸经由相应的酰基叠氮化物和治疗与所得的异氰酸酯的Curtius重排Ñ羟基琥珀酰亚胺。

  DOI：

  10.1016/s0040-4039(99)02353-9
• 作为产物：
  描述：

  在 sodium azide 作用下， 以 吡啶 、 水 、 甲苯 为溶剂， 反应 0.16h， 生成 succinimidyl {(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propyl}carbamate
  参考文献：
  名称：

  O-琥珀酰亚胺基-（9 H-芴-9-甲氧基羰基氨基）乙基氨基甲酸酯衍生物为活化单体的固相合成低聚尿素

  摘要：

  描述了使用O-琥珀酰亚胺基- （9 H-芴-9-基甲氧基羰基氨基）乙基氨基甲酸酯衍生物作为活化单体在固相载体上高效逐步合成寡聚脲（直至九聚体）的方法。这些构建块被容易地制备，起始自Ñ -Fmoc保护的β 3 -氨基酸经由相应的酰基叠氮化物和治疗与所得的异氰酸酯的Curtius重排Ñ羟基琥珀酰亚胺。

  DOI：

  10.1016/s0040-4039(99)02353-9

文献信息

• Novel urea oligomers, the preparation method thereof and pharmaceutical composition containing same
  申请人：Guichard Francois Roger Gilles

  公开号：US20050038105A1

  公开（公告）日：2005-02-17

  Compounds having a general formula X-(A)n-Y, wherein: n varies between 6 and 20; X denotes a hydrogen atom, an RaCO, RaOCO, RaNHCO or RaSO2 group, Ra being an alkyl, alkenyl, alkynyl, aryl, aralkyl, heteroaryl group, the groups being substituted or not, on condition that X is different from H when n is equal to 6; A denotes either a group having formula (I) or (II), wherein Ri is a hydrogen atom, an amino acid side chain, an alkyl, alkenyl, alkynyl, aryl, aralkyl or heteroaryl group, said groups being substituted or not, i being an integer of between 1 and n; Y is an NRbRc, Rb and Rc group having the same meaning as given earlier for Ra. The compounds are used for the preparation of medicaments that are intended to treat bacterial, fungal or cytotoxic diseases and, in particular, fungal infections, such as aspergillosis and candidiasis, and resistant bacterial infections.

  化合物的一般公式为X-(A)n-Y，其中：n在6到20之间变化；X表示氢原子，RaCO，RaOCO，RaNHCO或RaSO2基团，Ra是烷基，烯基，炔基，芳基，芳烷基，杂环芳基基团，这些基团被取代或未被取代，条件是当n等于6时，X与H不同；A表示具有式（I）或（II）的基团，其中Ri是氢原子，氨基酸侧链，烷基，烯基，炔基，芳基，芳烷基或杂环芳基基团，这些基团被取代或未被取代，i是1到n之间的整数；Y是NRbRc，其中Rb和Rc基团与Ra具有相同的含义。这些化合物用于制备用于治疗细菌，真菌或细胞毒性疾病的药物，特别是用于治疗真菌感染，如曲霉病和念珠菌病以及耐药细菌感染。
• Helix-Forming Oligoureas: Temperature-Dependent NMR, Structure Determination, and Circular Dichroism of a Nonamer with Functionalized Side Chains
  作者：Christine Hemmerlin、Michel Marraud、Didier Rognan、Roland Graff、Vincent Semetey、Jean-Paul Briand、Gilles Guichard

  DOI：10.1002/1522-2675(200211)85:11<3692::aid-hlca3692>3.0.co;2-w

  日期：2002.11

  To further investigate the degree of structural homology between gamma-peptides A and NX-Iinked oligoureas B, we prepared oligourea nonamer 2 containing Ala, Val, Leu, Phe, Tyr and Lys side chains. Oligomer 2 was synthesized on solid support from activated monomers, i.e., from enantiomerically pure succinimidyl (2-[(9H-fluoren-9-ylmethoxy)carbonyl]amino) ethyl)carbamates 3a-f that are further substituted at C(2) of the ethyl moiety. These precursors were conveniently prepared from N-Fmoc-protected beta(3)-amino acids with corresponding side chains. Detailed NMR studies (DQF-COSY, TOCSY, and ROESY) in (D-5)pyridine revealed that 2 adopts a regular (P)-2.5 helical secondary structure very similar to that previously determined for oligourea heptamer 1 and closely related to the (P)-2.6(14) helix of gamma-peptides. Temperature-dependent NMR further demonstrated the conformational homogeneity and remarkable stability of the structure of 2 in pyridine. The CD spectrum of 2 (0.2 mm) was recorded in MeOH with the aim to gain more information about the conformation of oligoureas. In contrast to 2.6-helical gamma-peptides, which display only a weak or no Cotton effect, oligourea 2 exhibits an intense positive Cotton effect at ca. 203 nm ([Theta] = + 373000 deg cm(2) dmol(-1)) that decreases only slowly upon increasing the temperature.
• Solid phase synthesis of oligoureas using O-succinimidyl-(9H-fluoren-9-ylmethoxycarbonylamino)ethylcarbamate derivatives as activated monomers
  作者：Gilles Guichard、Vincent Semetey、Marc Rodriguez、Jean-Paul Briand

  DOI：10.1016/s0040-4039(99)02353-9

  日期：2000.3

  An efficient stepwise synthesis of oligoureas (up to the nonamer) on solid support using O-succinimidyl-(9H-fluoren-9-ylmethoxycarbonylamino)ethylcarbamate derivatives as activated monomers is described. These building blocks were readily prepared starting from N-Fmoc-protected β3-amino acids via Curtius rearrangement of the corresponding acyl azides and treatment of the resulting isocyanate with

  描述了使用O-琥珀酰亚胺基- （9 H-芴-9-基甲氧基羰基氨基）乙基氨基甲酸酯衍生物作为活化单体在固相载体上高效逐步合成寡聚脲（直至九聚体）的方法。这些构建块被容易地制备，起始自Ñ -Fmoc保护的β 3 -氨基酸经由相应的酰基叠氮化物和治疗与所得的异氰酸酯的Curtius重排Ñ羟基琥珀酰亚胺。