diethyl 2-(ethoxycarbonyl)-2-formamido-4-methylene-6-<(tert-butoxycarbonyl)amino>-1,7-heptanedioate | 100910-42-7

• 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: diethyl 2-(ethoxycarbonyl)-2-formamido-4-methylene-6-<(tert-butoxycarbonyl)amino>-1,7-heptanedioate
• 英文别名: Triethyl 1-formamido-3-methylene-5-(tert-butoxycarbonylamino)-1,1,5-pentanetricarboxylate；triethyl 1-formamido-3-methylidene-5-[(2-methylpropan-2-yl)oxycarbonylamino]pentane-1,1,5-tricarboxylate
• CAS: 100910-42-7
• 化学式: C₂₁H₃₄N₂O₉
• 分子量: 458.509
• InChiKey: HSTGMBQAPRCWDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  32
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  146
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  diethyl 2-(ethoxycarbonyl)-2-formamido-4-methylene-6-<(tert-butoxycarbonyl)amino>-1,7-heptanedioate 生成 Diethyl 6-(tert-butoxycarbonylamino)-2-formamido-4-methylene-heptanedioate
  参考文献：
  名称：

  AGOURIDAS, CONSTANTIN;DAMAIS, CHANTAL;FAUVEAU, PATRICK

  摘要：

  DOI：
• 作为产物：
  描述：

  Triethyl 1-(formylamino)-5-(methanesulfonyloxy)-3-methylene-1,1,5-pentane tricarboxylate 在 Lindlar's catalyst sodium azide 、 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 diethyl 2-(ethoxycarbonyl)-2-formamido-4-methylene-6-<(tert-butoxycarbonyl)amino>-1,7-heptanedioate
  参考文献：
  名称：

  The lysine pathway as a target for a new genera of synthetic antibacterial antibiotics?

  摘要：

  Unsaturated analogues of diaminopimelic acid have been synthesized. The amino acids were designed so that they would be reversible or irreversible inhibitors of both of the two last enzymes of the lysine pathway. The compounds were tested with meso-diaminopimelate decarboxylase. trans-3,4-Didehydrodiaminopimelic acid (2) was found to be the most potent inhibitor. The antibacterial activities did not correlate with enzyme inhibiting activities. 4-Methylenediaminopimelic acid 4 showed strong antibacterial properties. It is suggested that L,L-diaminopimelate epimerase could be the target enzyme.

  DOI：

  10.1021/jm00156a021

文献信息

• Glutamic acid derivatives
  申请人：Roussel Uclaf

  公开号：US05108990A1

  公开（公告）日：1992-04-28

  All isomeric forms and mixtures of isomers of glutamic acid compounds of the formula ##STR1## wherein the glutamic acid of D- or L- configuration, R.sub.1 is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, an amino acid, a peptide of 2 to 4 amino acids and an amino acid or a peptide of 2 to 4 amino acids in which the amine is esterified with an optionally unsaturated aliphatic carboxylic acid of 6 to 24 carbon atoms or R.sub.1 is selected from the group consisting of a residue of a C.sub.6 -C.sub.24 optionally unsaturated aliphatic acid, R.sub.5 is selected from the group consisting of hydrogen or an alkyl radical of 1 to 5 carbon atoms, R.sub.3 is selected from the group consisting of hydroxy, alkoxy of 1 to 5 carbon atoms, an amino acid with the amine optionally substituted with alkyl of 1 to 5 carbon atoms, Z is ##STR2## R.sub.2 is selected from the group consisting of hydrogen, an amino acid and a peptide of 2 to 4 amino acids, R.sub.4 is selected from the group consisting of hydroxy, alkoxy 1 to 5 carbon atoms and an amino acid optionally substituted on the amine with alkyl of 1 to 5 carbon atoms, U is selected from the group consisting of ##STR3## --CH.dbd.CH--CH.sub.2 -- (E or Z isomer), --CH.sub.2 --CH.dbd.CH-- (E or Z isomer) and ##STR4## or U and Y together are .dbd.CH--CH.sub.2 --CH.sub.2 -- (E or Z isomer) and X is hydrogen or U and X together are .dbd.CH--CH.sub.2 --CH.sub.2 -- (E or Z isomer) and Y is hydrogen and their salts with non-toxic, pharmaceutically acceptable acid or bases having immunomodulatory properties.

  所有谷氨酸化合物的同分异构体和异构体混合物，其化学式为##STR1##其中D或L构型的谷氨酸，R.sub.1选自以下组：氢，1至5个碳原子的烷基，氨基酸，2至4个氨基酸的肽以及氨基酸或2至4个氨基酸的肽，其中胺基与6至24个碳原子的可选不饱和脂肪酸酯化或R.sub.1选自以下组：C.sub.6-C.sub.24可选不饱和脂肪酸的残基，R.sub.5选自以下组：氢或1至5个碳原子的烷基基团，R.sub.3选自以下组：羟基，1至5个碳原子的烷氧基，氨基酸，其胺基可选用1至5个碳原子的烷基取代，Z为##STR2## R.sub.2选自以下组：氢，氨基酸和2至4个氨基酸的肽，R.sub.4选自以下组：羟基，1至5个碳原子的烷氧基和氨基酸，其胺基可选用1至5个碳原子的烷基取代，U选自以下组：##STR3## --CH.dbd.CH--CH.sub.2 --（E或Z异构体），--CH.sub.2--CH.dbd.CH--（E或Z异构体）和##STR4##或U和Y一起为.dbd.CH--CH.sub.2--CH.sub.2--（E或Z异构体），X为氢或U和X一起为.dbd.CH--CH.sub.2--CH.sub.2--（E或Z异构体），Y为氢及其与非毒性、药学上可接受的酸或碱的盐，具有免疫调节作用。
• AGOURIDAS, CONSTANTIN;DAMAIS, CHANTAL;FAUVEAU, PATRICK
  作者：AGOURIDAS, CONSTANTIN、DAMAIS, CHANTAL、FAUVEAU, PATRICK

  DOI：——

  日期：——
• AGOURIDAS, C.;GIRODEAU, J. -M.;PINEAU, R.;LE, GOFFIC, F.
  作者：AGOURIDAS, C.、GIRODEAU, J. -M.、PINEAU, R.、LE, GOFFIC, F.

  DOI：——

  日期：——
• US5108990A
  申请人：——

  公开号：US5108990A

  公开（公告）日：1992-04-28
• The lysine pathway as a target for a new genera of synthetic antibacterial antibiotics?
  作者：Jean Marc Girodeau、Constantin Agouridas、Maryse Masson、Roland Pineau、Francois Le Goffic

  DOI：10.1021/jm00156a021

  日期：1986.6

  Unsaturated analogues of diaminopimelic acid have been synthesized. The amino acids were designed so that they would be reversible or irreversible inhibitors of both of the two last enzymes of the lysine pathway. The compounds were tested with meso-diaminopimelate decarboxylase. trans-3,4-Didehydrodiaminopimelic acid (2) was found to be the most potent inhibitor. The antibacterial activities did not correlate with enzyme inhibiting activities. 4-Methylenediaminopimelic acid 4 showed strong antibacterial properties. It is suggested that L,L-diaminopimelate epimerase could be the target enzyme.