β-(2-thienyl)-L-alanine methyl ester hydrochloride | 137490-86-9

• 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: β-(2-thienyl)-L-alanine methyl ester hydrochloride
• 英文别名: β-2-thienylalanine methyl ester hydrochloride；methyl (S)-2-amino-3-(thiophen-2-yl)propanoate hydrochloride；(S)-2-amino-3-[2]thienyl-propionic acid methyl ester; hydrochloride；(S)-2-Amino-3-[2]thienyl-propionsaeure-methylester; Hydrochlorid；3-(thien-2-yl)-DL-alanine methyl ester hydrochloride；3-(2-thienyl)-DL-alanine methyl ester hydrochloride；3-(2-thienyl)-L-alanine, methylester hydrochloride；(S)-Methyl 2-amino-3-(thiophen-2-yl)propanoate HCl；methyl (2S)-2-amino-3-thiophen-2-ylpropanoate;hydrochloride
• CAS: 137490-86-9
• 化学式: C₈H₁₁NO₂S*ClH
• 分子量: 221.708
• InChiKey: JOTSVOSIVDVLQL-FJXQXJEOSA-N

物化性质

• 熔点：
  174 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.21
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  β-(2-thienyl)-L-alanine methyl ester hydrochloride 在 盐酸 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 L-leucinyl-L-β-2-thienylalanine methyl ester hydrochloride
  参考文献：
  名称：

  相邻基团对疏水结合热力学的影响：疏水效应增加了复杂的方面

  摘要：

  使用等温滴定量热法（ITC）对在浅疏水口袋中结合的配体侧链进行系统修饰的热力学后果进行了评估，无论是否存在相邻的配体羧酸酯基团。数据显示，羧酸盐可能会通过改变未结合状态和结合状态下水合水的H键/组织状态来显着改变这些修饰的相对热力学特征。发现该羧酸酯基团在某些情况下是前焓的，对熵的，而在另一些情况下是反焓的，对熵的。还观察到了显着的焓-熵补偿关系，这反映了疏水作用受相关水环境的热力学状态支配的事实。

  DOI：

  10.1021/jm401609a
• 作为产物：
  描述：

  (S)-2-acetylamino-3-[2]thienyl-propionic acid p-toluidide 在 盐酸 作用下， 生成 β-(2-thienyl)-L-alanine methyl ester hydrochloride
  参考文献：
  名称：

  Dunn, Journal of Biological Chemistry, 1959, vol. 234, p. 802,803

  摘要：

  DOI：

文献信息

• Substituted Dihydroisoquinolinones by Iodide-Promoted Cyclocarbonylation of Aromatic α-Amino Acids
  作者：Mostafa M. Amer、Ana C. Carrasco、Daniel J. Leonard、John W. Ward、Jonathan Clayden

  DOI：10.1021/acs.orglett.8b03551

  日期：2018.12.21

  of aromatic α-amino acids, on treatment with phosgene and potassium iodide, undergo a mild Bischler–Napieralski-style cyclocarbonylation reaction that generates a tricyclic lactam by insertion of a C═O group between amino acid nitrogen and the ortho position of the aryl substituent. Regio- and diastereoselective functionalization of the lactam generates a library of substituted dihydroisoquinolinones

  一系列芳香族 α-氨基酸的咪唑啉酮衍生物在用光气和碘化钾处理后，会发生温和的 Bischler-Napieralski 式环羰基化反应，通过在氨基酸氮和邻位之间插入 C=O 基团生成三环内酰胺。芳基取代基的位置。内酰胺的区域选择性和非对映选择性功能化产生了取代的二氢异喹啉酮及其对映体富集形式的同源物库。
• Inhibitors of protein isoprenyl transferases
  申请人：University of Pittsburgh

  公开号：US06310095B1

  公开（公告）日：2001-10-30

  Compounds having the formula or a pharmaceutically acceptable salt thereof wherein R1 is (a) hydrogen, (b) loweralkyl, (c) alkenyl, (d) alkoxy, (e) thioalkoxy, (f) halo, (g) haloalkyl, (h) aryl-L2—, and (i) heterocyclic-L2—; R2 is selected from (a) (b) —C(O)NH—CH(R14)—C(O)OR15, (d) —C(O)NH—CH(R14)—C(O)NHSO2R16, (e) —C(O)NH—CH(R14)-tetrazolyl, (f) —C(O)NH-heterocyclic, and (g) —C(O)NH—CH(R14)—C(O)NR17R18; R3 is substituted or unsubstituted heterocyclic or aryl, substituted or unsubstituted cycloalkyl or cycloalkenyl, and —P(W)RR3RR3′; R4 is hydrogen, lower alkyl, haloalkyl, halogen, aryl, arylakyl, heterocyclic, or (heterocyclic)alkyl; L1 is absent or is selected from (a) —L4—N(R5)—L5—, (b) —L4—O—L5—, (c) —L4—S(O)n—L5— (d) —L4—L6—C(W)—N(R5)—L5—, (e) —L4—L6—S(O)m—N(R5)—L5 —, (f) —L4—N(R5)—C(W)—L7—L5—, (g) —L4—N(R5)—S(O)p—L7—L5—, (h) optionally substituted alkylene, (i) optionally substituted alkenylene, (j) optionally substituted alkynylene (k) a covalent bond, (l) and (m) are inhibitors of protein isoprenyl transferases. Also disclosed are protein isoprenyl transferase inhibiting compositions and a method of inhibiting protein isoprenyl transferases.

  具有以下结构式或其药用可接受盐的化合物，其中R1为(a)氢，(b)较低烷基，(c)烯基，(d)烷氧基，(e)硫代烷氧基，(f)卤素，(g)卤代烷基，(h)芳基-L2—，和(i)杂环-L2—；R2选自(a) (b) —C(O)NH—CH(R14)—C(O)OR15，(d) —C(O)NH—CH(R14)—C(O)NHSO2R16，(e) —C(O)NH—CH(R14)-四唑基，(f) —C(O)NH-杂环，和(g) —C(O)NH—CH(R14)—C(O)NR17R18；R3为取代或未取代的杂环或芳基，取代或未取代的环烷基或环烯基，以及—P(W)RR3RR3′；R4为氢，较低烷基，卤代烷基，卤素，芳基，芳基烷基，杂环，或(杂环)烷基；L1为空缺或选自(a) —L4—N(R5)—L5—，(b) —L4—O—L5—，(c) —L4—S(O)n—L5—，(d) —L4—L6—C(W)—N(R5)—L5—，(e) —L4—L6—S(O)m—N(R5)—L5—，(f) —L4—N(R5)—C(W)—L7—L5—，(g) —L4—N(R5)—S(O)p—L7—L5—，(h)可选择取代的烷基，(i)可选择取代的烯基，(j)可选择取代的炔基，(k)共价键，(l)和(m)是蛋白异戊二烯基转移酶的抑制剂。还公开了蛋白异戊二烯基转移酶抑制剂组合物和抑制蛋白异戊二烯基转移酶的方法。
• New renin-inhibitory peptides and their use
  申请人：Sankyo Company, Limited

  公开号：US04698329A1

  公开（公告）日：1987-10-06

  Compounds of formula R.sup.1 CO--NH--CH(R.sup.2)--CONH--CH(R.sup.3)--X [wherein: R.sup.1 represents alkyl having an .alpha.-amino or protected .alpha.-amino substituent and an aryl, heterocyclic or heterocyclic-dithio substituent; R.sup.2 represents a variety of aliphatic and cycloaliphatic hydrocarbon groups, which may be substituted; R.sup.3 represents isobutyl, sec-butyl, benzyl or (C.sub.3 -C.sub.8 cycloalkyl)methyl; and X represents a group of formula --CH(--A--R.sup.4)--Y (in which: A represents a single bond or an alkylene group; R.sup.4 represents a carboxy group; a protected carboxy group, a carbamoyl group, an N-substituted carbamoyl group, a carbazoyl group, an N-substituted carbazoyl group or an acyl group; and Y represents a hydroxy group, a mercapto group or a formyl group), or a group of formula --P(O) (R.sup.5)--OH (in which R.sup.5 represents a substituted alkyl group having at least one substituent selected from carboxy groups, protected carboxy groups, N-substituted carbamoyl groups, carbazoyl groups, N-substituted carbazoyl groups, C.sub.2 -C.sub.7 aliphatic carboxylic acyl groups and aromatic carboxylic acyl groups)]; and their salts are renin inhibitors, which may be used in the treatment of angiotensin-induced hypertension.

  式为R.sup.1 CO--NH--CH(R.sup.2)--CONH--CH(R.sup.3)--X的化合物【其中：R.sup.1代表具有α-氨基或保护的α-氨基取代基和芳基、杂环基或杂环二硫基的烷基；R.sup.2代表多种脂肪和环脂烃基，可能被取代；R.sup.3代表异丁基、仲丁基、苄基或（C.sub.3 -C.sub.8环烷基）甲基；X代表式--CH(--A--R.sup.4)--Y的基团（其中：A代表单键或烷基基团；R.sup.4代表羧基、保护的羧基、氨基甲酰基、N-取代氨基甲酰基、氨基苯并噻唑基、N-取代氨基苯并噻唑基或酰基；Y代表羟基、巯基或甲酰基），或式--P(O) (R.sup.5)--OH的基团（其中R.sup.5代表取代的烷基基团，至少有一个取代基被选择自羧基、保护的羧基、N-取代氨基甲酰基、氨基苯并噻唑基、N-取代氨基苯并噻唑基、C.sub.2 -C.sub.7脂肪羧酰基和芳香族羧酰基）】及其盐是肾素抑制剂，可用于治疗由肾素引起的高血压。
• Benzyl compounds which inhibit leukocyte adhesion mediated by VLA-4
  申请人：——

  公开号：US20030065193A1

  公开（公告）日：2003-04-03

  Disclosed are compounds which bind VLA-4. Certain of these compounds also inhibit leukocyte adhesion and, in particular, leukocyte adhesion mediated by VLA-4. Such compounds are useful in the treatment of inflammatory diseases in a mammalian patient, e.g., human, wherein the disease may be, for example, asthma, Alzheimer's disease, atherosclerosis AIDS dementia, diabetes, inflammatory bowel disease, rheumatoid arthritis, tissue transplantation, tumor metastasis and myocardial ischemia. The compounds can also be administered for the treatment of inflammatory brain diseases such as multiple sclerosis.

  本发明涉及一种与VLA-4结合的化合物。其中某些化合物还能抑制白细胞粘附，特别是通过VLA-4介导的白细胞粘附。这些化合物可用于治疗哺乳动物患者（例如人类）的炎症性疾病，如哮喘、阿尔茨海默病、动脉硬化、艾滋病痴呆、糖尿病、炎症性肠病、类风湿性关节炎、组织移植、肿瘤转移和心肌缺血等疾病。这些化合物还可用于治疗多发性硬化等炎症性脑部疾病。
• Structure−Activity Relationships on Phenylalanine-Containing Inhibitors of Histone Deacetylase:  In Vitro Enzyme Inhibition, Induction of Differentiation, and Inhibition of Proliferation in Friend Leukemic Cells
  作者：Sybille Wittich、Hans Scherf、Changping Xie、Gerald Brosch、Peter Loidl、Clarissa Gerhäuser、Manfred Jung

  DOI：10.1021/jm0208119

  日期：2002.7.1

  Inhibitors of histone deacetylases (HDACs) are a new class of anticancer agents that affect gene regulation. We had previously reported the first simple synthetic HDAC inhibitors with in vitro activity at submicromolar concentrations. Here, we present structure-activity data on modifications of a phenylalanine-containing lead compound including amino acid amides as well as variations of the amino acid part. The compounds were tested for inhibition of maize HD-2, rat liver HDAC, and for the induction of terminal cell differentiation and inhibition of proliferation in Friend leukemic cells. In the amide series, in vitro inhibition was potentiated up to 15-fold, but the potential to induce cell differentiation decreased. Interestingly, an HDAC class selectivity was indicated among some of these amides. In the amino acid methyl ester series, a biphenylalanine derivative was identified as a good enzyme inhibitor, which blocks proliferation in the submicromolar range and is also a potent inducer of terminal cell differentiation.