methyl 2-aminopent-4-ynoate | 70837-20-6

• 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: methyl 2-aminopent-4-ynoate
• 英文别名: methyl 2-amino-4-pentynoate；propargyclycine methyl ester hydrochloride；propargyl glycine methyl ester；2-amino-pent-4-ynoic acid methyl ester；4-Pentynoic acid, 2-amino-, methyl ester
• CAS: 70837-20-6
• 化学式: C₆H₉NO₂
• 分子量: 127.143
• InChiKey: GHQXMDDXHKPECL-UHFFFAOYSA-N

物化性质

• 沸点：
  191.8±30.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-aminopent-4-ynoate 在 copper acetylacetonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 34.0h， 生成 methyl 2-{[4'-methoxy(1,1'-biphenyl)-4-yl]sulfonyl}amino-6-(morpholin-1N-yl)hex-4-ynoate
  参考文献：
  名称：

  Development of New Carboxylic Acid-Based MMP Inhibitors Derived from Functionalized Propargylglycines

  摘要：

  A series of carboxylic acids were prepared from a propargylglycine scaffold and tested for efficacy as matrix metalloproteinase (MMP) inhibitors. Detailed SAR for the series is reported for four enzymes within the MMP family. The inhibitors were typically potent against collagenase-3 (MMP-13) and gelatinase A (MMP-2), while they spared collagenase-1 (MMP-1) and only moderately inhibited stromelysin (MMP-3). Compound 40 represents a typical inhibition profile of a compound with reasonable potency. Introduction of polar groups was required in order to generate inhibitors with acceptable water solubility, and this often resulted in a loss of potency as in compound 63. High serum protein binding proved to be a difficult hurdle with many compounds such as 48 showing > 99% binding. Some compounds such as 64 displayed similar to 90% binding, but no reliable method was discovered for designing molecules with low protein binding. Finally, selected data regarding the pharmacokinetic behavior of these compounds is presented.

  DOI：

  10.1021/jm000477l
• 作为产物：
  描述：

  diethyl α-acetamido-α-propargylmalonate 在 盐酸 作用下， 生成 methyl 2-aminopent-4-ynoate
  参考文献：
  名称：

  Stereocontrolled total synthesis of (.+-.)-quinocarcin

  摘要：

  DOI：

  10.1021/ja00223a052

文献信息

• Non-peptidyl inhibitors of VLA-4 dependent cell binding useful in treating inflammatory, autoimmune, and respiratory diseases
  申请人：——

  公开号：US20020049236A1

  公开（公告）日：2002-04-25

  There is disclosed a genus of non-peptidyl compounds, wherein said compounds are VLA-4 inhibitors useful in treating inflammatory, autoimmune, and respiratory diseases, and wherein said compounds comprise a compound of Formula (1.0.0): 1 and pharmaceutically acceptable salts and other prodrug derivatives thereof, wherein: A is (C 1 -C 6 ) alkyl, cycloalkyl, aryl, heteroaryl or heterocyclyl optionally substituted with 0 to 3 R 9 ; or is a member selected from the group consisting of the following radicals: A 1 -NHC(═O)NH-A 2 -, A 1 -NHC(═O)O-A 2 -, A 1 -OC(═O)NH-A 2 -, A 1 -NHSO 2 NH-A 2 -, A 1 -NHC(═O)-A 2 -, A 1 -C(═O)NH-A 2 -, A 1 -NHSO 2 -A 2 -, A 1 -SO 2 NH-A 2 -, A 1 -(CH 2 ) r -A 2 -, where A 1 and A 2 are each independently selected from the group consisting of hydrogen, aryl, (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, cycloalkyl, heteroaryl, and heterocyclyl substituted with 0 to 3 R 9 ; B is a member independently selected from the group consisting of the following: 2 E is a single bond; —O—; —NR 10 —; —CH═CH—; —CC—; —S(═) q ; —CR 11 R 12 NR 10 —; or —CR 11 R 12 ; X is —O—; —C(═O)—; —S(═O) q —; or —NR 10 —; X 1 , X 2 and X 3 are each independently selected from the group consisting of CH, CR 9 or N; Y is a single bond; —C(═O)—; —C(═S)—; or —S(═O) 2 —; R 7 is (C 1 -C 6 ) alkyl; (CH 2 ) k OR 5 ; (CH 2 ) k NR 6 C(═O)R 5 ; (CH 2 ) k NR 6 C(═O)OR 5 ; (CH 2 ) k NR 6 SO 2 R 5 ; (CH 2 ) k NR 6 R 5 ; F; CF 3 ; OCF 3 ; aryl, substituted with 0 to 3 R 9 ; heterocyclyl, substituted with 0 to 3 R 9 ; heteroaryl, substituted with 0 to 3 R 9 ; cycloalkyl, substituted with 0 to 3 R 9 ; or R 7 may be taken together with R 8 to form a cycloalkyl or heterocyclyl ring; or R 7 may be taken together with R 11 to form a cycloalkyl or heterocyclyl ring; and R 8 is hydrogen; F; (C 1 -C 6 ) alkyl or (C 1 -C 6 ) alkoxy.

  本发明涉及一类非肽类化合物，其中这些化合物是VLA-4抑制剂，用于治疗炎症性、自身免疫和呼吸道疾病，这些化合物包括如下式（1.0.0）的化合物： 1 以及其药学上可接受的盐和其他前药衍生物，其中： A为（C 1 -C 6 ）烷基，环烷基，芳基，杂芳基或杂环烷基，可选地取代为0至3个R 9 ；或者是从以下基团中选择的成员：A 1 -NHC(═O)NH-A 2 -，A 1 -NHC(═O)O-A 2 -，A 1 -OC(═O)NH-A 2 -，A 1 -NHSO 2 NH-A 2 -，A 1 -NHC(═O)-A 2 -，A 1 -C(═O)NH-A 2 -，A 1 -NHSO 2 -A 2 -，A 1 -SO 2 NH-A 2 -，A 1 -(CH 2 ) r -A 2 -，其中A 1 和A 2 各自独立地选择自氢，芳基，（C 1 -C 6 ）烷基，（C 2 -C 6 ）烯基，（C 2 -C 6 ）炔基，环烷基，杂芳基和杂环烷基，取代为0至3个R 9 ； B是独立地从以下成员中选择的： 2 E是单键；—O—；—NR 10 —；—CH═CH—；—CC—；—S(═) q ；—CR 11 R 12 NR 10 —；或—CR 11 R 12 ； X是—O—；—C(═O)—；—S(═O) q —；或—NR 10 —；X 1 ，X 2 和X 3 各自独立地选择自CH，CR 9 或N；Y是单键；—C(═O)—；—C(═S)—；或—S(═O) 2 —；R 7 是（C 1 -C 6 ）烷基；（CH 2 ） k OR 5 ；（CH 2 ） k NR 6 C(═O)R 5 ；（CH 2 ） k NR 6 C(═O)OR 5 ；（CH 2 ） k NR 6 SO 2 R 5 ；（CH 2 ） k NR 6 R 5 ；F；CF 3 ；OCF 3 ；芳基，取代为0至3个R 9 ；杂环烷基，取代为0至3个R 9 ；杂芳基，取代为0至3个R 9 ；环烷基，取代为0至3个R 9 ；或R 7 可以与R 8 一起形成环烷基或杂环烷基环；或R 7 可以与R 11 一起形成环烷基或杂环烷基环；而R 8 是氢；F；（C 1 -C 6 ）烷基或（C 1 -C 6 ）烷氧基。
• New oxybenzamide derivatives useful for inhibiting factor Xa or VIIa
  申请人：——

  公开号：US20020198195A1

  公开（公告）日：2002-12-26

  The present invention relates to compounds comprising the following formula: R 0 —Q—X—Q′—W—U—V—G—M  (I) These compounds are useful as pharmacologically active compounds. They exhibit an antithrombotic effect and are suitable, for example, for the therapy and prophylaxis of cardiovascular disorders such as thromboembolic diseases or restenoses. These compounds are reversible inhibitors of the blood clotting enzymes factor Xa (FXa) and/or factor VIIa (FVIIa), and can generally be used to treat, prevent, or cure conditions in which an undesired activity of factor Xa and/or factor VIIa is present, or where inhibition of factor Xa and/or factor VIIa is intended. The invention further relates to processes for the preparation of these compounds, methods of their use (e.g., as active ingredients in pharmaceuticals), and pharmaceutical preparations comprising them.

  本发明涉及包含以下公式的化合物： R 0 —Q—X—Q′—W—U—V—G—M  (I) 这些化合物作为药物活性化合物是有用的。它们展现出抗血栓作用，并适用于例如治疗和预防心血管疾病，如血栓栓塞性疾病或再狭窄。这些化合物是血液凝固酶因子Xa（FXa）和/或因子VIIa（FVIIa）的可逆性抑制剂，通常可用于治疗、预防或治愈存在因子Xa和/或因子VIIa不期望活性的情况，或旨在抑制因子Xa和/或因子VIIa的情况。本发明还涉及制备这些化合物的方法、它们的使用方法（例如，作为药品中的活性成分）以及包含它们的药物制剂。
• INHIBITION AND DISPERSION OF BACTERIAL BIOFILMS WITH IMIDAZOLE-TRIAZOLE DERIVATIVES
  申请人：Melander Christian

  公开号：US20090263438A1

  公开（公告）日：2009-10-22

  Disclosure is provided for imidazole-triazole derivative compounds that prevent, remove and/or inhibit the formation of biofilms, compositions comprising these compounds, devices comprising these compounds, and methods of using the same.

  披露了咪唑-三唑衍生物化合物，用于防止、移除和/或抑制生物膜的形成，包含这些化合物的组合物，包含这些化合物的设备，以及使用这些化合物的 methods。
• Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester imines
  作者：Zara M Seibel、Jeffrey S Bandar、Tristan H Lambert

  DOI：10.3762/bjoc.17.134

  日期：——

  A procedure for the enantioselective synthesis of α-substituted glutamates and pyroglutamates via a cyclopropenimine-catalyzed Michael addition of amino ester imines is described. Enantioselectivities of up to 94% have been achieved, and a variety of functional groups were found to be compatible. The impact of the catalyst structure and imine substitution is discussed. Compared to other methods, this protocol allows for a broader and more enantioselective access to pyroglutamate derivatives.

  通过环丙烯亚胺催化的氨基酯亚胺的迈克尔加成，描述了一种合成α-取代谷氨酸和吡咯谷氨酸的对映选择性程序。已经实现了高达94%的对映选择性，并发现多种官能团是兼容的。讨论了催化剂结构和亚胺取代的影响。与其他方法相比，这种方案允许更广泛和更对映选择性地获得吡咯谷氨酸衍生物。
• [EN] INHIBITION AND DISPERSION OF BIOFILMS IN PLANTS WITH IMIDAZOLE-TRIAZOLE DERIVATIVES<br/>[FR] INHIBITION ET DISPERSION DE BIOFILMS DANS DES PLANTES AVEC DÉRIVÉS D'IMIDAZOLE-TRIAZOLE
  申请人：UNIV NORTH CAROLINA STATE

  公开号：WO2010077603A1

  公开（公告）日：2010-07-08

  Disclosure is provided for methods of preventing, removing or inhibiting microbial biofilm formation or microbial infection in a plant or plant part thereof, including applying thereto a treatment effective amount of an active compound as described herein, or an agriculturally acceptable salt thereof. Methods of enhancing a microbicide (e.g., including a copper, antibiotic, bacteriophage, etc.) and/or plant defense activator are also provided, including applying an active compound as described herein. Compositions comprising an active compound as described herein in an agriculturally acceptable carrier are also provided, and in some embodiments the compositions further include a microbicide (e.g., including copper, antibiotic, bacteriophage, etc.) and/or plant defense activator.

  本公开提供了一种防止、去除或抑制植物或植物部分中微生物生物膜形成或微生物感染的方法，包括向其施加根据本文所述的有效化合物或其农业可接受的盐的治疗有效量。还提供了增强微生物杀灭剂（例如，包括铜、抗生素、细菌噬菌体等）和/或植物防御激活剂的方法，包括施加本文所述的有效化合物。还提供了包含本文所述的有效化合物在农业可接受载体中的组合物，有些实施例中，这些组合物进一步包括微生物杀灭剂（例如，包括铜、抗生素、细菌噬菌体等）和/或植物防御激活剂。