benzyl Boc-4-iodophenylalanine | 129150-58-9

• 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: benzyl Boc-4-iodophenylalanine
• 英文别名: N-[tert-butyl-carbonyl]-4-iodo-L-phenylalanine phenylmethyl ester；benzyl (2S)-3-(4-iodophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 129150-58-9
• 化学式: C₂₁H₂₄INO₄
• 分子量: 481.33
• InChiKey: WMXFVQYEFNNROZ-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl Boc-4-iodophenylalanine 在 sodium perborate 、 sodium hydroxide 、 四(三苯基膦)钯 、 2,6-二叔丁基-4-甲基苯酚 、 硼烷 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 15.0h， 生成 (S)-2-((tert-butoxycarbonyl)amino)-3-(4-(2-hydroxyethyl)phenyl)propionic acid
  参考文献：
  名称：

  Structure-Based Design, Synthesis, and Biological Evaluation of Irreversible Human Rhinovirus 3C Protease Inhibitors. 2. Peptide Structure−Activity Studies

  摘要：

  The structure-based design, chemical synthesis, and biological evaluation of various peptide-derived human rhinovirus (HRV) 3C protease (3CP) inhibitors are described. These compounds are comprised of an ethyl propenoate Michael acceptor moiety and a tripeptidyl binding determinant. The systematic modification of each amino acid residue present in the binding determinant as well as the N-terminal functionality is described. Such modifications are shown to provide irreversible HRV-14 3CP inhibitors with anti-3CP activities (k(obs)/[I]) ranging from 60 to 280 000 M-1 s(-1) and antiviral EC50's which approach 0.15 mu M. An optimized inhibitor which incorporates several improvements identified by the structure-activity studies is also described. This molecule displays very rapid irreversible inhibition of HRV-14 3CP (k(obs)/[I] = 800 000 M-1 s(-1)) and potent antiviral activity against HRV-14 in cell culture (EC50 = 0.056 mu M). A 1.9 Angstrom crystal structure of an S-alkylthiocarbamate-containing inhibitor complexed with HRV-8 3CP is also detailed.

  DOI：

  10.1021/jm9800696
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 potassium hydrogencarbonate 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 benzyl Boc-4-iodophenylalanine
  参考文献：
  名称：

  Synthesis of optically active arylene bis-alanine derivatives carrying orthogonal protecting groups

  摘要：

  Derivatives of para- and meta-phenylene bis-alanine and related biphenyl systems, carrying four orthogonal protecting groups, were synthesised via combinations of Heck couplings and asymmetric hydrogenations, The intermediate unsaturated arylalanine derivatives were hydrogenated using [Rh(COD)((R,R)-DIPAMP)]+BF4- or [Rh(COD)(Me-DuPHOS)]X-+(-) as catalysts to produce the optically active, protected amino acid derivatives in greater than or equal to 98% e.e. as analysed by chiral phase HPLC. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00014-7

文献信息

• Production method for biarylalanine
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20040024229A1

  公开（公告）日：2004-02-05

  There is provided a production method for producing a biarylalanine compound of formula (4): 1 wherein R 1 represents a amino protective group and R 2 represents an amino protective group or a hydrogen atom, R 3 is a carboxy protective group, or the like, and R 4 is a substituted or unsubstituted aryl or heteroaryl group, characterized by reacting an aromatic amino acid of formula (1) 2 wherein X is a halogen atom or a trifluoromethanesulfonyloxy group, and R 1 , R 2 and R 3 has the same meaning as defined above, with an organic boron compound of formula (2): 3 wherein R 4 has the same meaning as defined above, and Q 1 and Q 2 are the same or different and each is a hydroxy group, an alkoxy group having 1 to 4 carbon atom(s), in the presence of nickel catalyst and a base.

  提供一种生产生产式（4）的联苯丙氨酸化合物的生产方法： 其中R1代表氨基保护基，R2代表氨基保护基或氢原子，R3是羧基保护基等，R4是取代或未取代的芳基或杂芳基，其特征在于将式（1）的芳香族氨基酸： 其中X是卤素原子或三氟甲磺氧基团，R1、R2和R3的含义与上述定义相同，与式（2）的有机硼化合物反应： 其中R4的含义与上述定义相同，Q1和Q2相同或不同，每个都是羟基、具有1至4个碳原子的烷氧基，在镍催化剂和碱的存在下。
• Viral polymerase inhibitors
  申请人：——

  公开号：US20020065418A1

  公开（公告）日：2002-05-30

  A compound of the formula I: 1 wherein: X is CH or N; Y is O or S; Z is OH, NH 2 , NMeR 3 , NHR 3 ; OR 3 or 5- or 6-membered heterocycle, having 1 to 4 heteroatoms selected from 0, N and S, said heterocycle being optionally substituted with from 1 to 4 substituents; A is N, COR 7 or CR 5 , wherein R 5 is H, halogen, or (C 1-6 ) alkyl and R 7 is H or (C 1-6 alkyl), with the proviso that X and A are not both N; R 6 is H, halogen, (C 1-6 alkyl) or OR 7 , wherein R 7 is H or (C 1-6 alkyl); R 1 is selected from the group consisting of 5- or 6-membered heterocycle having 1 to 4 heteroatoms selected from O, N, and S, phenyl, phenyl(C 1-3 )alkyl, (C 2-6 )alkenyl, phenyl(C 2-6 )alkenyl, (C 3-6 )cycloalkyl, (C 1-6 )alkyl, CF 3 , 9- or 10-membered heterobicycle having 1 to 4 heteroatoms selected from O, N and S, wherein said heterocycle, phenyl, phenyl(C 2-6 )alkenyl and phenyl(C 1-3 )alkyl), alkenyl, cycloalkyl, (C 1-6 )alkyl, and heterobicycle are all optionally substituted with from 1 to 4 substituents R 2 is selected from (C 1-6 )alkyl, (C 3-7 )cycloalkyl, (C 3-7 )cycloalkyl(C 1-3 )alkyl, (C 6-10 )bicycloalkyl, adamantyl, phenyl, and pyridyl, all of which is optionally substituted with from1 to 4 substituents; R 3 is selected from H, (C 1-6 )alkyl, (C 3-6 )cycloalkyl, (C 3 6 )cycloalkyl(C 1-6 )alkyl, (C 6-10 )aryl, (C 6-10 )aryl(C 1-6 )alkyl, (C 2-6 )alkenyl, (C 3-6 )cycloalkyl(C 2-6 )alkenyl, (C 6-10 )aryl(C 2-6 )alkenyl, N{(C 1-6 )alkyl} 2 , NHCOO(C 1-6 )alkyl(C 6-10 )aryl, NHCO(C 6-10 )aryl, (C 1-6 )alkyl-5- or 10-atom heterocycle, having 1 to 4 heteroatoms selected from O, N and S, and 5- or 10-atom heterocycle having 1 to 4 heteroatoms selected from O, N and S; wherein said alkyl, cycloalkyl, aryl, alkenyl and heterocycle are all optionally substituted with from 1 to 4 substituents; n is zero or 1; or a detectable derivative or salt thereof. The compounds of the invention may be used as inhibitors of hepatitis C virus replication. The invention further provides a method for treating or preventing hepatitis C virus infection.

  该化合物的结构式为I:1，其中：X为CH或N；Y为O或S；Z为OH、NH2、NMeR3、NHR3、OR3或含有1至4个异原子（0、N和S）的5-或6-成员杂环，该杂环可选择性地与1至4个取代基取代；A为N、COR7或CR5，其中R5为H、卤素或（C1-6）烷基，R7为H或（C1-6）烷基，但X和A不能同时为N；R6为H、卤素、（C1-6）烷基或OR7，其中R7为H或（C1-6）烷基；R1选自包括含有1至4个异原子（O、N和S）的5-或6-成员杂环、苯基、苯基（C1-3）烷基、（C2-6）烯基、苯基（C2-6）烯基、（C3-6）环烷基、（C1-6）烷基、CF3、含有1至4个异原子（O、N和S）的9-或10-成员杂环的群体，其中该杂环、苯基、苯基（C2-6）烯基和苯基（C1-3）烷基、烯基、环烷基、（C1-6）烷基和杂环均可选择性地与1至4个取代基取代；R2选自（C1-6）烷基、（C3-7）环烷基、（C3-7）环烷基（C1-3）烷基、（C6-10）双环烷基、金刚烷基、苯基和吡啶基，所有这些基均可选择性地与1至4个取代基取代；R3选自H、（C1-6）烷基、（C3-6）环烷基、（C3-6）环烷基（C1-6）烷基、（C6-10）芳基、（C6-10）芳基（C1-6）烷基、（C2-6）烯基、（C3-6）环烷基（C2-6）烯基、（C6-10）芳基（C2-6）烯基、N(C1-6)烷基2、NHCOO(C1-6)烷基（C6-10）芳基、NHCO（C6-10）芳基、（C1-6）烷基-含有1至4个异原子（O、N和S）的5-或10-原子杂环和含有1至4个异原子（O、N和S）的5-或10-原子杂环；其中所述烷基、环烷基、芳基、烯基和杂环均可选择性地与1至4个取代基取代；n为零或1；或其可检测衍生物或盐。该发明的化合物可用作乙型肝炎病毒复制的抑制剂。该发明还提供了一种治疗或预防乙型肝炎病毒感染的方法。
• ANTIMICROBIAL COMPOUNDS
  申请人：Stensen Wenche

  公开号：US20110301076A1

  公开（公告）日：2011-12-08

  The present invention relates to a compound of formula (I) AA-AA-AA-R 1 —R 2 (I) wherein, in any order, 2 of said AA (amino acid) moieties are cationic amino acids and 1 of said AA is an amino acid with a lipophilic R group, the R group having 14-27 non-hydrogen atoms; R 1 is a N atom, which may be substituted by a branched or unbranched C 1 -C 10 alkyl or aryl group, which group may incorporate up to 2 heteroatoms selected from N, O and S; and R 2 is an aliphatic moiety having 2-20 non-hydrogen atoms, said moiety being linear, branched or cyclic. The invention further relates to formulations containing these compounds, solid supports having these compounds attached thereto, the use of these compounds in therapy, particularly as antimicrobial, anti-tumour or anti-biofilm agents and non-therapeutic uses of these compounds, particularly their use in inhibiting biofilm formation or removing a biofilm.

  本发明涉及一种具有以下结构的化合物(I) AA-AA-AA-R1—R2(I)，其中，任意顺序中，所述的2个AA（氨基酸）基团是带正电的氨基酸，而1个AA是带有亲脂性R基团的氨基酸，所述R基团具有14-27个非氢原子；R1是一个N原子，可以被支链或非支链的C1-C10烷基或芳基取代，该基团最多可以包含2个从N、O和S中选择的杂原子；R2是具有2-20个非氢原子的脂肪族基团，该基团是直链、支链或环状的。该发明还涉及含有这些化合物的配方、固体支持物上附着这些化合物、这些化合物在治疗中的使用，特别是作为抗微生物、抗肿瘤或抗生物膜剂，以及这些化合物的非治疗用途，特别是它们在抑制生物膜形成或去除生物膜中的应用。
• Methods of peptide modification
  申请人：Stensen Wenche

  公开号：US09212202B2

  公开（公告）日：2015-12-15

  The present invention relates to a method of improving the resistance of a peptide or peptidomimetic to degradation by trypsin which comprises incorporating into said peptide or peptidomimetic a C-terminal capping group of formula (I): X—Y—Z (I) wherein X is a N atom, which may be substituted by a branched or unbranched C1-C10 alkyl or aryl group which group may incorporate up to 2 heteroatoms selected from N, O and S; Y represents a group selected from —Ra—Rb—, —Ra—Rb—Rb,- and —Rb—Rb—Ra— wherein Ra is C, O, S or N, and Rb is C; each of Ra and Rb, may be substituted by C1-C4 alkyl groups or unsubstituted; and Z is a group comprising 1 to 3 cyclic groups each of 5 or 6 non-hydrogen atoms, 2 or more of the cyclic groups may be fused and one or more of the cyclic groups may be substituted; the Z. moiety incorporates a maximum of 15 non-hydrogen atoms; and wherein the bond between Y and Z is a covalent bond between Ra or Rb of Y and a non-hydrogen atom of one of the cyclic groups of Z.

  本发明涉及一种改善肽或肽类似物对胰蛋白酶降解抗性的方法，包括将式(I)的C-末端封端基团（C-terminal capping group）引入到所述肽或肽类似物中：X—Y—Z（I），其中X是一个N原子，可能被一种支链或非支链的C1-C10烷基或芳基取代，该基团可包含最多2个从N、O和S中选择的杂原子；Y代表从—Ra—Rb—、—Ra—Rb—Rb-和—Rb—Rb—Ra—中选择的一个基团，其中Ra是C、O、S或N，Rb是C；每个Ra和Rb可能被C1-C4烷基基团或未取代基团取代；Z是一个包含1至3个每个由5或6个非氢原子组成的环基团的基团，其中2个或更多的环基团可以融合，一个或多个环基团可以被取代；Z基团包含最多15个非氢原子；并且Y和Z之间的键是Y的Ra或Rb与Z的一个环基团的非氢原子之间的共价键。
• [EN] ANTIMICROBIAL FORMULATIONS COMPRISING SILICONE<br/>[FR] FORMULATIONS ANTIMICROBIENNES COMPRENANT DU SILICONE
  申请人：AMICOAT AS

  公开号：WO2021250286A1

  公开（公告）日：2021-12-16

  The present invention provides a controlled release formulation comprising a silicone substrate which comprises a compound of Formula (I): AA-AA-AA-X-Y. The invention further provides methods of making these formulations, medical devices such as dressings incorporating said formulations and medical uses thereof.

  本发明提供了一种控制释放的配方，包括一个硅基底物，该底物包括式(I)的化合物：AA-AA-AA-X-Y。本发明还提供了制备这些配方的方法，包括将该配方用于制作敷料的医疗器械和医疗用途。